Antitumoral effects of triazole and hydrazide-hydrazone derivative hybrid molecules and their synthesis methods.

Abstract

The invention relates to hydrazide and hydrazone derivative antitumor molecules bearing a 1,2,4-triazole ring, acting on the MCF-7 breast cancer cell line and exhibiting cyclooxygenase-1 (COX-1), with a particularly selective inhibitory effect on the cyclooxygenase-2 (COX-2) enzyme, and to the synthesis methods of these molecules. The general structure of the molecules subject to the invention is shown by Formula X.

Description

1 TARIFF ANTITUMURAL EFFECTIVE TRIAZOLE AND HYDRAZIDE-HYDRAZONE DERIVATIVE HYBRID MOLECULES AND THE METHODS OF SYNTHESIS OF THESE MOLECULES Technical Field to Which the Invention Relates The invention was developed on the MCF-7 breast cancer cell line and cyclooxygenase-1 (COX-1) 5 effective on, specifically, selective inhibition of the cyclooxygenase-2 (COX-2) enzyme. hydrazide and hydrazide-hydrazone derivatives that have the activity and carry a 1,2,4-triazole ring. It deals with molecules that have antitumor effects and the methods of synthesizing these molecules. State of the Art Inflammation is the immune system's response to various diseases or injuries that affect the body. It is a response that the body creates to protect itself. When tissue homeostasis is disrupted, Macrophages and mast cells produce bioactive substances such as cytokines, chemokines, ROS, and histamine. It releases stimuli, and this is associated with the inflammatory process. This causes leukocyte mobilization and leakage at the site of injury [1]. Prolonged responses lead to chronic inflammation and cancer 15 It results in many diseases, primarily [2, 3]. Clinical and epidemiological Studies have shown a strong link between chronic infection, inflammation, and cancer. This shows that acute and chronic inflammation can lead to atherosclerosis, heart disease, cancer, and arthritis. (joint inflammation), metabolic syndrome, high blood pressure, Parkinson's disease, Alzheimer's disease, It causes many diseases such as asthma, inflammatory bowel disease and diabetes. It is possible. In the current state of the technique, non-steroidal anti-inflammatory drugs (NSAIDs) are used to inhibit inflammation. Anti-inflammatory drugs (NSAIDs) are used. The target of these drugs... Cyclooxygenase (COX) enzymes, one of which consists of three isoforms, are involved in pain management. It is an enzyme targeted in the removal and treatment of inflammation. One of the COX isoforms is 25 Cyclooxygenase-2 (COX-2) contributes to the modulation of multiple procarcinogenic effects. a prostaglandin endoperoxide synthase responsible for the formation of prostanoids found It is enzyme number 2. In many types of cancer, this enzyme is overexpressed and acts as a marker. It has been shown that it is used in carcinogenesis as a result of excessive expression of COX-2. It is encouraged, increasing cancer recurrence and invasion, and survival rate is 30. It reduces the rate and makes cancer cells resistant to radiotherapy and chemotherapy. 2 This leads to increased COX-1, bicarbonate and mucus secretion, and gastric... reduced acid and pepsin secretion and adequate blood flow to the mucosa PGE2 and other cytoprotective agents exhibit cytoprotective effects on various aspects of gastric function. It is an enzyme responsible for the synthesis of PGI2[4]. COX is included in the current technique. Examples of inhibitors include celecoxib, indomethacin, metamizol, aspirin, and aminopyrine 5. It can be given. Although current techniques offer significant advantages in cancer treatment or prevention... nonsteroidal anti-inflammatory drugs (NSAIDs) that are of significant importance Although anti-inflammatory drugs have been developed, inflammation inhibition alone is not sufficient. It is not effective enough in treating cancer. Because, effective treatment against cancer is 10 In the last 30 years, significant progress has been made in the development of protocols for some types of cancer. Despite the progress made, when looking at the overall success rate over the five-year period... It appears that the desired level of progress in terms of survival has not been achieved. This The current situation and the increasing incidence of cancer worldwide necessitate new approaches to cancer treatment. This necessitates the development of new approaches. 15 In the current state of technology, the most common type of cancer diagnosed in women is breast cancer. It is cancer and is the second leading cause of death among women worldwide. [5]. Scientific research conducted on the treatment of breast cancer with current techniques. studies based on research conducted on the MCF-7 breast cancer cell line It is being carried out. The 1,2,4-triazole ring, MCF-20, has many pharmacological activities. Studies are currently underway to measure their effects on 7 breast cancer cell lines. It is possible to encounter them in technology. In fact, in the literature, hydrazide and hydrazone derivatives are mentioned. the activity of molecules containing these substances in the MCF-7 breast cancer cell line Studies aimed at measurement are also included. A study conducted by Yurii G. SAMELIUK and colleagues examined 25 fields in medicine and pharmacy. The efficacy of 1,2,4-triazole derivatives has been measured. In the aforementioned scientific study, 1,2,4- The molecules studied, which contain a triazole ring, showed anticancer properties. This is stated, and particularly regarding their effectiveness on MCF-7 cells. is mentioned[6]. In the current technique, although it plays a very important role in cancer treatment and immunity 30 the body's system to protect itself against various diseases and injuries Nonsteroidal anti-inflammatory drugs (NSAIDs) aimed at inhibiting inflammation, a reaction caused by a viral infection. 3 Although anti-inflammatory drugs (NSAIDs) exist, these drugs are particularly... There is not enough research on breast cancer, one of the deadliest types of cancer today. It does not have an active function. In the known state of the art, the 1,2,4-triazole ring Studies to measure the effects on the MCF-7 breast cancer cell line. Although ongoing, the molecules synthesized in these studies are believed to reduce pain. the elimination and treatment of inflammation target the overexpression of COX enzymes They do not possess the ability to block. In other words, these molecules Even though they are effective against the MCF-7 breast cancer cell line, they cause an overexpression of COX enzymes. Since they cannot inhibit its expression, carcinogenesis will be stimulated, leading to cancer. The recurrence rate and invasion will be increased, and the survival rate of cancer patients will be 10. The rates will decrease, and worst of all, cancer cells will become less resistant to radiotherapy and chemotherapy. It will have become resistant. This is included in the state of the art, and especially in the treatment of breast cancer. limitations and deficiencies of the drugs used or molecules synthesized, existing The technique involves the development of a 1,2,4-triazole derivative, 15, for use in the treatment of breast cancer. Even though the molecules were effective on the MCF-7 breast cancer cell line, COX their inability to prevent the overexpression of enzymes and therefore carcinogenesis encouraging it increases the recurrence rate and invasion of cancer, thus Cancer patients' survival rates are decreasing and cancer cells are being treated with radiotherapy. and fatal consequences such as becoming resistant to chemotherapy 20 Due to problems such as these, it is effective both on the MCF-7 breast cancer cell line and... It has an inhibitory effect on COX-1 and COX-2 isoenzymes, cancer A new molecule is needed for use in its treatment. Brief Description and Objectives of the Invention 25 In the invention, the MCF-7 breast cancer cell line and cyclooxygenase-1 (COX-1) effective on, specifically, selective inhibition of the cyclooxygenase-2 (COX-2) enzyme. hydrazide and hydrazide-hydrazone derivatives that have the activity and carry a 1,2,4-triazole ring. Antitumor molecules and their synthesis methods are described. The general structure of the molecules involved in the invention is represented by Formula X. 30 4 Formula X One aim of the invention is to use it in cancer treatment, and specifically in MCF-7 breast cancer. The goal is to identify molecules that are effective against cancer cell lines. The molecules identified were hydrazide and hydrazide-5, which carry a 1,2,4-triazole ring. Hydrazone derivatives with antitumor effects are obtained through synthesis methods. Effect of the molecules discussed in the invention on the MCF-7 breast cancer cell line. The mechanism involves applying different concentrations of substances to MCF-7 at specific times. This is understood by measuring its inhibition on the cell line. Another objective of the invention is to have an activity on the COX-1 isoenzyme, and specifically 10 It has a selective inhibitory effect on the cyclooxygenase-2 (COX-2) enzyme. The goal is to develop molecules. The development of these molecules involves 1,2,4-triazole. hydrazide and hydrazide-hydrazone derivative molecules with antitumor effects that carry a ring It is obtained through synthesis methods. The invention was developed on both the MCF-7 breast cancer cell line and cyclooxygenase-1 (COX-1) 15 It is effective on and particularly selective on the cyclooxygenase-2 (COX-2) enzyme. Molecules with inhibitory activity are being identified. These molecules... The identification of hydrazide and hydrazide-hydrazone derivatives bearing a 1,2,4-triazole ring. This is achieved through the synthesis of molecules with antitumor effects. With this invention... Radiotherapy increases the survival rates of cancer patients and reduces cancer cells. and the emergence of molecules that prevent them from becoming resistant to chemotherapy The aim is to identify these molecules, namely 1,2,4-triazole. hydrazide and hydrazide-hydrazone derivative molecules with antitumor effects that carry a ring This is achieved through synthesis. The molecules that are the subject of the invention are one of the COX isoforms. and whose overexpression promotes tumor formation, i.e., carcinogenesis 25 which increases the rate of cancer recurrence and invasion, and reduces the survival rate of cancer patients. reducing the survival rate and making cancer cells resistant to radiotherapy and chemotherapy It provides inhibition of COX-2, which causes this condition. Explanation of the Figures Figure 1. Molecules related to the invention and cisplatin and osimertinib used as standards. Showing the effect of 24-hour application on the viability of MCF-7 cells. comparative bar chart Figure 2. Molecules related to the invention and cisplatin and osimertinib 5 used as standards. the effect of 24-hour application of the substances on the viability of HEK293 cells comparative bar graph showing Figure 3. Fourier Transform Infrared Spectroscopy (FTIR) spectrum of Formula 1. Figure 4. 1H-NMR spectrum of Formula 1. Figure 5. 13C-NMR (APT) spectrum of Formula 1. Figure 6. ESI-HRMS spectrum of Formula 1 (negative) Figure 7. FTIR spectrum of formula 2a. Figure 8. 1H-NMR spectrum of formula 2a. Figure 9. 13C-NMR (APT) spectrum of formula 2a. Figure 10. ESI-HRMS spectrum of Formula 2a (positive) 15 Figure 11. ESI-HRMS spectrum of Formula 2a (negative) Figure 12. FTIR Spectrum of Formula 2b. Figure 13. 1H-NMR Spectrum of Formula 2b. Figure 14. 13C-NMR (APT) spectrum of Formula 2b. Figure 15. ESI-HRMS spectrum of Formula 2b (positive) 20 Figure 16. ESI-HRMS spectrum of Formula 2b (negative) Figure 17. FTIR Spectrum of Formula 2c. Figure 18. 1H-NMR Spectrum of Formula 2c. Figure 19. 13C-NMR (APT) spectrum of formula 2c. Figure 20. ESI-HRMS spectrum of formula 2c (positive) 25 Figure 21. ESI-HRMS spectrum of Formula 2c (negative) 6 Figure 22. FTIR Spectrum of Formula 2d. Figure 23. 1H-NMR Spectrum of Formula 2d. Figure 24. 13C-NMR (APT) spectrum of formula 2d. Figure 25. ESI-HRMS spectrum of formula 2d (positive) Figure 26. ESI-HRMS spectrum of formula 2d (negative) 5 Figure 27. FTIR Spectrum of Formula 2e. Figure 28. 1H-NMR Spectrum of Formula 2e. Figure 29. 13C-NMR (APT) spectrum of formula 2e. Figure 30. ESI-HRMS spectrum of formula 2e (positive) Figure 31. ESI-HRMS spectrum of formula 2e (negative) 10 Figure 32. FTIR Spectrum of Formula 2f. Figure 33. 1H-NMR Spectrum of Formula 2f. Figure 34. 13C-NMR (APT) spectrum of formula 2f. Figure 35. ESI-HRMS spectrum of formula 2f (positive) Figure 36. ESI-HRMS spectrum of formula 2f (negative) 15 Figure 37. FTIR Spectrum of Formula 2g. Figure 38. 1H-NMR Spectrum of Formula 2g. Figure 39. 13C-NMR (APT) spectrum of formula 2g. Figure 40. ESI-HRMS spectrum of formula 2g (positive) Figure 41. ESI-HRMS spectrum of formula 2g (negative) 20 Figure 42. FTIR Spectrum of Formula 2h. Figure 43. 1H-NMR Spectrum of Formula 2h. Figure 44. 13C-NMR (APT) spectrum of formula 2h. Figure 45. ESI-HRMS spectrum of formula 2h (positive) 7 Figure 46. ESI-HRMS spectrum of formula 2h (negative) Figure 47. FTIR Spectrum of Formula 2i. Figure 48. 1H-NMR Spectrum of Formula 2i. Figure 49. 13C-NMR (APT) spectrum of formula 2i. Figure 50. ESI-HRMS spectrum of Formula 2i (positive) 5 Figure 51. ESI-HRMS spectrum of Formula 2i (negative) Figure 52. FTIR Spectrum of Formula 2j. Figure 53. 1H-NMR Spectrum of Formula 2j. Figure 54. 13C-NMR (APT) spectrum of formula 2j. Figure 55. ESI-HRMS spectrum of formula 2j (positive) 10 Figure 56. ESI-HRMS spectrum of formula 2j (negative) Figure 57. FTIR Spectrum of Formula 2k. Figure 58. 1H-NMR Spectrum of Formula 2k. Figure 59. 13C-NMR (APT) spectrum of formula 2k. Figure 60. ESI-HRMS spectrum of formula 2k (positive) 15 Figure 61. ESI-HRMS spectrum of formula 2k (negative) Figure 62. FTIR Spectrum of Formula 2l. Figure 63. 1H-NMR Spectrum of Formula 2l. Figure 64. 13C-NMR (APT) spectrum of formula 2l. Figure 65. ESI-HRMS spectrum of Formula 2l (positive) 20 Figure 66. ESI-HRMS spectrum of Formula 2l (negative) Figure 67. FTIR Spectrum of Formula 2m. Figure 68. 1H-NMR Spectrum of Formula 2m. Figure 69. 13C-NMR (APT) spectrum of formula 2m. 8 Figure 70. ESI-HRMS spectrum of formula 2m (positive) Figure 71. ESI-HRMS spectrum of formula 2m (negative) Figure 72. FTIR Spectrum of Formula 2n. Figure 73. 1H-NMR Spectrum of Formula 2n. Figure 74. 13C-NMR (APT) spectrum of formula 2n 5 Figure 75. ESI-HRMS spectrum of formula 2n (positive) Figure 76. ESI-HRMS spectrum of formula 2n (negative) Figure 77. FTIR Spectrum of Formula 20. Figure 78. 1H-NMR Spectrum of Formula 2O. Figure 79. 13C-NMR (APT) spectrum of Formula 2O 10 Figure 80. ESI-HRMS spectrum of Formula 2o (positive) Figure 81. ESI-HRMS spectrum of Formula 2o (negative) Figure 82. FTIR Spectrum of Formula 2p. Figure 83. 1H-NMR Spectrum of Formula 2p. Figure 84. 13C-NMR (APT) spectrum of formula 2p 15 Figure 85. ESI-HRMS spectrum of formula 2p (positive) Figure 86. ESI-HRMS spectrum of formula 2p (negative) Figure 87. FTIR Spectrum of Formula 2r. Figure 88. 1H-NMR Spectrum of Formula 2r. Figure 89. 13C-NMR (APT) spectrum of formula 2r 20 Figure 90. ESI-HRMS spectrum of formula 2r (positive) Figure 91. ESI-HRMS spectrum of formula 2r (negative) Figure 92. FTIR Spectrum of Formula 2s. Figure 93. 1H-NMR Spectrum of Formula 2s. 9 Figure 94. 13C-NMR (APT) spectrum of formula 2s. Figure 95. ESI-HRMS spectrum of formula 2s (positive) Figure 96. ESI-HRMS spectrum of formula 2s (negative) Figure 97. FTIR Spectrum of Formula 2t. Figure 98. 1H-NMR Spectrum of Formula 2t 5 Figure 99. 13C-NMR (APT) spectrum of formula 2t. Figure 100. ESI-HRMS spectrum of formula 2t (positive) Figure 101. ESI-HRMS spectrum of formula 2t (negative) Detailed Description of the Invention 10 The invention was developed on the MCF-7 breast cancer cell line and cyclooxygenase-1 (COX-1) effective on, specifically, selective inhibition of the cyclooxygenase-2 (COX-2) enzyme. hydrazide and hydrazide-hydrazone derivatives that have the activity and carry a 1,2,4-triazole ring. It relates to molecules with antitumor effects and methods of synthesizing these molecules. The general structure of molecules is represented by Formula X. 15 Formula X Here, R is selected from the following formulas; Ri= -HN NH2 , Ri In the case where the Rı group in Formula X is Rı = -HN NH2, then 2- is obtained. [[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide molecule This is represented by Formula 1. 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide 5 (Formula 1) Formula 1 It is obtained as a white powder with a yield of 60-95% and its melting point is 166- It is in the range of 168°C. 10 - Fourier Transform Infrared Spectroscopy (FTIR) ν (cm-1): 3317, 3257 (NH stretching band); 3152, 3043 (ar CH stretching band); 2900, 2850 (aldehyde C- H (asymmetric and symmetrical stress band), 1679 (C=O stress band); 1610 (hydrazone C=N stretching band), 1506 (aromatic C=C stretching, amide II NH bending) and CN stretching combination bands); 1429, 1398 (aldehyde CH asymmetric and 15 symmetrical stretch band); 1215 (CS stretch band), 1205 (aromatic CF stretch band) band), 837 (1,4-disubstituted aromatic CH stretching band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 9.37 (s, 1H, CONH); 7.77 (d, J: 1.6 Hz, 1H, furan C5-H); 7.63-7.59 (m, 2H, FPhC2,6-H); 7.47 (t, J: 8.65 Hz, 2H, FPhC3,5-H); 6.54 (dd, J: 3.5; 1.6 Hz, 1H, furan C4-H); 6.24 (d, J: 3.5 Hz, 1H, 20 furan C3-H); 4.32 (s, 2H, NH2); 3.88 (s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 166.43, 163.22 (d, J: 252 Hz), 151.8, 148.01, 145.34, 141.40, 130.71 (d, J: 9.5 Hz), 130.06 (d, J: 3 Hz), 117.47 (d, J: 22 Hz), 112.15, 111.8, 34.9 - ESI-HRMS: mass: m / z 333.0695 calculated [M+K]+; m / z 372.0332 found 25 [M+K]+: m / z 372.0943; Calculated for C14H12FN5O2S: 50.44 %C 3.63 %H 21.01%N, Found: 50.31%C 3.82%H 21.03%N. 11 In the formula X in question, the group Rı must be Rı = . In this case, molecular derivatives represented by Formula 2a-t are obtained. Formula Molecules denoted by 2a-t are 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- They are [il]sulfanil]-N'-[(substituted phenyl)methylidene]acetohydrazide derivatives. Formula 2a-t In Formula 2a-t, the R1 group is selected from among the formulas listed below. is selected; -H 10 Formula a Formula b Formula c Formula d Rıı 12 Formula e Formula f Formula g Formula h Formula i Formula j Formula k Formula l Formula m Formula n Formula o Formula p Formula r Formula s Formula t 13 The molecules with the formula 2a-t are as follows:  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'- [(phenyl)methylidene]acetohydrazide (Formula 2a)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,3- [dihydroxyphenyl)methylidene]acetohydrazide (Formula 2b) 5  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-4- diethylaminophenyl)methyldene]acetohydrazide (Formula 2c)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-3- methoxyphenyl)methyldene]acetohydrazide (Formula 2d)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-10 ethylphenyl)methyldene]acetohydrazide (Formula 2e)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,4- dinitrophenyl)methyldene]acetohydrazide (Formula 2f)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4,5- trimethoxyphenyl)methyldene]acetohydrazide (Formula 2g) 15  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- nitrophenyl)methyldene]acetohydrazide (Formula 2x)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- methylphenyl)methylidene]acetohydrazide (Formula 2i)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4-20 dimethoxyphenyl)methyldene]acetohydrazide (Formula 2h)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- methoxy)methyldene]acetohydrazide (Formula 2k)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- cyanophenyl)methyldene]acetohydrazide (Formula 2l) 25  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- hydroxyphenyl)methyldene]acetohydrazide (Formula 2m)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(3- hydroxyphenyl)methyldene]acetohydrazide (Formula 2n)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-30 [chlorphenyl]methylidene]acetohydrazide (Formula 2o)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- [florphenyl)methylidene]acetohydrazide (Formula 2p) 14  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- [bromphenyl)methylidene]acetohydrazide (Formula 2r)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2- [hydroxyphenyl)methylidene]acetohydrazide (Formula 2s)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-5 [dimethylaminophenyl]methylidene]acetohydrazide (Formula 2t) 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(phenyl)methylidene] acetohydrazide (Formula 2a) When R1=-H in the aforementioned Formula 2a-t, the molecule represented by Formula 2a is obtained. is being done. Formula 2a It is obtained as a white powder with a yield of 60-95% and its melting temperature is... It is in the range of 119-121°C. - FTIR ν (cm-1): 3419 (NH stretching band), 3177, 3086 (aromatic CH stretching band) (band), 2964 (aldehyde CH asymmetric and symmetric stretching band), 1670 (amide C=O (stretch band), 1600 (hydrazone C=N stretch band), 1509 (aromatic C=C 20 strain, amide II NH bending and CN strain combination bands), 1403, 1383 (aldehyde CH asymmetric and symmetric stretch band), 1223 (CS stretch band), 1202 (aromatic CF stretching band), 841 (1,4-disubstituted aromatic CH stretching band) band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.73 and 11.68 (2s, 1H, CONH); 8.19 25 and 8.01 (2s, 1H, N=CH); 7.77 (d, J: 1.8 Hz, 1H, furan C5-H); 7.49-7.42 (m, 9H, aromatic CH); 6.53 (dd, J: 3.4; 1.8 Hz, 1H, furan C4-H); 6.23 (d, J: 3.4 Hz, 1H, furan C3-H); 4.48 and 4.07 (2s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.90 and 163.74 (C=O); 163.21 (d, J: 248 H); 151.95; 147.85; 147.65 and 144.41 (C=N); 145.32; 141.38; 134.36; 130.69 (d, J: 9.17 Hz); 130.47; 130.13 (d, J: 3 Hz); 129.28; 127.33; 5 117.46 (d, J: 23 Hz); 112.13; 111.80; 35.68 and 35.61 - ESI-HRMS: mass: m / z 421.1008, calculated [M+H]+: m / z 422.1087 [M+H]+: m / z 422.1091, calculated [MH]+: m / z 420.0930, found [MH]+: m / z Calculated for 420.0946; C21H16FN5O2S.0.5H2O: 58.59%C 3.98%H 16.27%N, Found: 58.17%C 3.909%H 15.79%N. 10 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,3-dihydroxy [phenyl)methylidene]acetohydrazide (Formula 2b) In Formula 2a-t, when Rıı = , the molecule is represented by Formula 2b. is obtained. 15 H Formula 2b It is obtained as a white powder with a yield of 60-95%. Melting temperature. It is in the range of 190-192.5°C. 20 - FTIR ν (cm-1): 3509 (OH stretch band), 3169 (NH stretch band), 3028 (ar CH stretching band), 2970, 2928, 2855 (aldehyde CH asymmetric and symmetric stretching 16 1682 (amide C=O stretching band), 1578 (hydrazone C=N stretching band), 1509 (combination of aromatic C=C stretching, amide II NH bending and CN stretching) bands), 1449, 1359 (aldehyde CH asymmetric and symmetric stretch band), 1225 (CS stretching band), 1158 (aromatic CF stretching band), 842 (1,4-disubstituted aromatic CH stretch band); 5 - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.98 and 11.62 (2s, 1H, CONH); 10.75 (br.s., 1H, OH); 9.56 (br.s., 1H, OH); 8.38 and 8.31 (2s, 1H, N=CH); 7.78 (d, J: 1.8 Hz, 1H, furan C5-H); 7.64–7.60 (m, 2H, FPhC2,6-H); 7.47 (td, J: 8.73; 2.09 Hz; 2H, FPhC3,5-H); 7.1 (d, J: 7.8, 1H aromatic C6-H); 6.85 (d, J: 7.8, 1H, aromatic C4–H); 6.68 (t, J: 7.8 Hz, 1H, aromatic C5-H); 6.54 (dd J: 3.3; 1.8 Hz, 10 1H, furan C4–H); 6.24 (d, J: 3.3 Hz, 1H, furan C3-H); 4.47 and 4.09 (2s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.46 and 163.60 (C=O); 163.2 (d, J: 248 Hz); 151.99; 148.57 and 142.78 (C=N); 147.83; 146.44; 146.03; 145.38; 141.37; 130.69 (d, J: 9.04 Hz); 130.11 (d, J: 2.76 Hz); 120.27; 119.67; 119.17; 117.92; 117.18; 117.49 (d, J: 23.29 Hz); 112.16; 111.80; 35.74 and 35.35 15 - ESI-HRMS: kütle: m / z 453.0907, hesaplanan [M+H]+: m / z 454.0985, month [M+H]+: m / z 454.0990, calculated [MH]+: m / z 452.0828, found [MH]+: m / z Calculated for 452.0845; C21H16FN5O4S.0.5H2O: 54.54%C 3.71%H 15.14%N, Found: 54.76%C 3.547%H 15.21%N. 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-4-diethyl [aminophenyl)methylidene]acetohydrazide (Formula 2c) When Rıı = in Formula 2a-t, then Formula 2c applies. The molecule shown is obtained. 25 17 Formula 2c It is obtained as a white powder with a yield of 60-95% and melting point. Its temperature is in the range of 247-249°C. 5 - FTIR ν (cm-1): 3183 (NH stretch band), 3051 (ar CH stretch band), 2976, 2932, 2870 (aldehyde CH asymmetric and symmetric stretching band), 1664 (amide C=O (stretch band), 1600 (hydrazone C=N stretch band), 1509 (aromatic C=C strain, amide II NH bending and CN strain combination bands), 1356 (aldehyde CH (asymmetric and symmetric stretch band) 1224 (CS stretch band), 1197 10 (aromatic CF stretching band), 848 (1,4-disubstituted aromatic CH stretching band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.66 and 11.33 (2s, 1H, CONH); 11,10 (s, 1H, OH); 8.18 and 8.11 (2s, 2H, N=CH); 7.77 (d, J = 1.8 Hz, 1H, furan C5-H); 7.63-7.60 (m, 2H, FPhC2,6-H); 7.47 (t, J: 8.7 Hz, 2H, FPhC3.5-H); 7.21 (d, J: 8.92 Hz, 1H, aromaticC6-H); 6.54 (dd, J = 3.54; 1.8 Hz, 1H, furan C4-H); 6.22-6.27 15 (m, 2H, furan C3-H and aromaticC5-H), 6.10 (d, J: 2.4 Hz, 1H, aromaticC3-H); 4.41 and 4.01 (2s, 2H, SCH2); 3.35 (N-CH2CH3, with DMSO peaks); 1.1 (t, J: 7.0 Hz, 6H, 2N-CH2CH3) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 167.60 and 162.70 (C=O); 163.22 (d, J: 248 Hz); 160.02; 151.69; 149.62 and 144.22 (C=N); 150.69; 147.93; 20 145.38; 141.33; 131.93; 130.71 (d, J: 9.36 Hz); 130.01 (d, J: 3.2 Hz); 117.48 (d, J: 23 Hz); 112.15; 111.85; 106.64; 104.14; 97.84; 44.26; 35.80 and 35.35; 12.99 - ESI-HRMS: mass: m / z 508.1692, calculated [M+H]+: m / z 509.1771, found [M+H]+: m / z 509.1781, calculated [MH]+: m / z 507.1614, found [MH]+: m / z Calculated for 507.1629; C25H25FN6O3S: 59.04%C 4.95%H 16.52%N, 25 Findings: 58.70%C 5.095%H 16.49%N. 18 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-3-methoxy [phenyl)methylidene]acetohydrazide (Formula 2d) In Formula 2a-t, when Rıı = , Formula 2d 5 The molecule shown is obtained. Formula 2d It is obtained as a white powder with a yield of 60-95% and has a melting point of 10. It is in the range of 211-214oC. - FTIR ν (cm-1): 3534 (OH stretch band), 3162 (NH stretch band), 3063 (ar CH stretching band), 2974, 2930, 2838 (aldehyde CH asymmetric and symmetric stretching 1674 (amide C=O stretching band), 1605 (hydrazone C=N stretching band), 1511 (aromatic C=C stretching, amide II NH bending and CN stretching combination 15 bands), 1456, 1382 (aldehyde CH asymmetric and symmetric stretch band), 1226 (CS stretch band), 1184 (aromatic CF stretch band), 849 (1,4-disubstituted aromatic CH stretch band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.92 and 11.60 (2s, 1H, CONH); 10.57 20 (s, 1H, OH); 8.40 and 8.32 (2s, 2H, N=CH); 7.77 (d, J: 1.7 Hz, 1H, furan C5-H); 7.63-7.60 (m, 2H, FPhC2,6-H); 7.47 (td, 2H, J: 8.81, 2.15 Hz, FPhC3,5-H); 7.15 19 (dd, J: 8; 1.3 Hz, aromatic C6-H); 7.03 (dd, J: 8, 1.3 Hz, aromatic C4-H); 6.85 (t, J: 8 Hz, aromatic C5-H); 6.51 (dd, J: 3.6, 1.7 Hz, 1H, furan C4-H); 6.21 (d, J: 3.6 Hz, 1H, furan C3-H); 4.44 and 4.05 (2s, 2H, SCH2); 3.79 (s, 3H, OCH3) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.57 and 163.56 (C=O); 5 163.21 (d, J: 248 Hz); 151.97; 151.65; 148.46; 147.82; 147.54 and 141.66 (C=N); 145.32; 141.31; 130.71 (d, J: 9.13 Hz); 130.14 (d, J: 2.76 Hz); 120.87; 119.54; 119.36; 117.46 (d, J: 23 Hz); 114.25; 112.15; 111.87; 56.31; 35.69 and 35.3 - ESI-HRMS: mass: m / z 467.1063, calculated [M+H]+: m / z 468.1141, found 10 [M+H]+: m / z 468.1148, calculated [MH]+: m / z 466.0985, found [MH]+: m / z Calculated for 466.1000; C22H18FN5O4S.0,5 C2H5-OH: 56.32%C 4.32%H 14.28%N, Found: 56.00%C 4.508%H 14.24%N 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-ethylphenyl)methylidene] 15 acetohydrazide (Formula 2e) In Formula 2a-t, when Rıı = , it is represented by Formula 2e. molecules are obtained. NN N HE F S HE NH N CH3 Formula 2e It is obtained as a white powder with a yield of 60-95% and melting point. Its temperature is in the range of 190-192.5°C. - FTIR ν (cm-1): 3172, 3113 (NH stretch band), 3077 (ar CH stretch band), 2962, 2932, 2872 (aldehyde CH asymmetric and symmetric stretching band), 1672 (amide C=O stretching band), 1617 (hydrazone C=N stretching band), 1508 (aromatic C=C 5 strain, amide II NH bending and CN strain combination bands), 1473, 1430, 1383 (aldehyde CH asymmetric and symmetric stretch band), 1222 (CS stretch band), 1154 (aromatic CF stretching band), 832 (1,4-disubstituted aromatic CH stretch band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.62 (s, 1H, CONH); 8.15 and 7.98 10 (2s, 1H, N=CH); 7.78 (d, J: 1.7 Hz, 1H, furan C5-H); 7.63-7.59 (m, 2H, FPhC2,6- H); 7.57 (d, J: 8.11 Hz, 2H, aromatic C2,6-H); 7.47 (td, 2H, J: 8.76, 2.4 Hz, FPhC3,5-H); 7.28 (d, J: 8.11 Hz, 2H, aromatic C3,5-H); 6.54 (dd, J: 3.6, 1.7 Hz, 1H, furan C4-H); 6.22 (d, J: 3.6 Hz, 1H, furan C3-H); 4.46 and 4.06 (2s, 2H, SCH2); 2.65 (with Ar-CH2-CH3, DMSO peaks); 1.19 (t, J: 7.58 Hz, 3H, Ar-CH2-15 CH3) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.77 and 163.56 (C=O); 163.2 (d, J: 248 Hz); 151.95; 147.84; 147.63 and 144.44 (C=N); 146.51; 145.34; 141.39; 131.92; 130.71 (d, J: 9.41 Hz); 130.15 (d, J: 3.14 Hz); 128.71; 127.40; 117.46 (d, J: 23.15 Hz); 112.13; 111.76; 35.67 and 35.62; 28.55; 15.82 20 - ESI-HRMS: mass: m / z 449.1321, calculated [M+H]+: m / z 450.1400, found [M+H]+: m / z 450.1406, calculated [MH]+: m / z 448.1243, found [MH]+: m / z 448.1259; C23H20FN5O2S. Calculated for 0.5 C2H5-OH: 61%C 4.91%H 14.82%N, Found: 60.71%C 4.877%H 15.09%N. 30 21 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,4-dinitrophenyl) [methylidene]acetohydrazide (Formula 2f) In Formula 2a-t, when Rıı = , it is represented by Formula 2f. The molecule is obtained. 5 NN N HE F S HE NH N N + HE – HE N + HE – HE Formula 2f It is synthesized as a yellow powder with a yield of 60-95% and its melting temperature is... It is in the range of 121-123.5°C. 10 - FTIR ν (cm-1): 3470 (NH stretch band), 3089 (ar CH stretch band), 2933, 2833 (aldehyde CH asymmetric and symmetric stretching band), 1681 (amide C=O stretching band) band), 1599 (hydrazone C=N stretching band), 1544 (NITRO structure belonging to NO asymmetric stretching band), 1509 (aromatic C=C stretching, amide II NH bending and C- N stretching combination bands), 1438 (aldehyde CH asymmetric and symmetric 15 1339 (symmetrical stretch band of nitro structure NO), 1225 (C- S-stretch band), 1153 (aromatic CF-stretch band), 838 (1,4-disubstituted aromatic CH stretching band). - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 12.36 and 12.18 (2s, 1H, CONH); 8.78 (s, 1H, aromatic C3-H); 8.55 (d, 1H, J: 8.65 Hz, aromaticC5-H); 8.32 (d, 1H, J: 20 8.65 Hz, aromaticC6-H); 8.67 and 8.47 (2s, 1H, N=CH); 7.77 (s, 1H, furan C5-H); 22 7.63–7.60 (m, 2H, FPhC2,6-H); 7.48 (t, J: 8.72 Hz, 2H, FPhC3,5-H); 6.53 (s, 1H, furan C4–H); 6.20 (s, 1H, furan C3-H); 4.48 and 4.12 (2s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 169.54 and 164.54 (C=O), 163.22 (d, J: 248.28 Hz), 151.60, 148.02, 147.87, 147.65, 145.35, 141.60 and 138.38 (C=N), 141.32, 134.32, 130.68 (d, J: 9.19 Hz), 130.09 (d, J: 2.98 Hz), 5 129.98, 127.99, 120.78, 117.49 (d, J: 23.51 Hz), 112.11, 111.80, 35.59 and 35.30 - ESI-HRMS: kütle: m / z 511.0710, hesaplanan [M+H]+: m / z 512.0788, month [M+H]+: m / z 512.0797, calculated [MH]+: m / z 510.0632, found [MH]+: m / z Calculated for 510.0648; C21H14FN7O6S.0.5 C2H5-OH: 49.44%C 3.21%H 18.34%N, Found: 49.45%C 3.224%H 18.27%N. 10 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4,5-trimethoxy [phenyl)methylidene]acetohydrazide (Formula 2g) In the aforementioned Formula 2a-t, when Rıı = , it is represented by Formula 2g. The molecule is obtained. 15 NN N HE F S HE NH N HE HE HE CH3 CH3 CH3 Formula 2g It is synthesized as a white powder with a yield of 60-95% and melting point. Its temperature is between 176-179°C. 20 - FTIR ν (cm-1): 3148 (NH stretch band), 3072 (ar CH stretch band), 2978, 2935, 2872 (aldehyde CH asymmetric and symmetric stretching band), 1650 (amide C=O (stretch band), 1600 (hydrazone C=N stretch band), 1509 (aromatic C=C 23 strain, amide II NH bending and CN strain combination bands), 1436, 1372 (aldehyde CH asymmetric and symmetric stretch band), 1223 (CS stretch band), 1125 (aromatic CF stretching band), 846 (1,4-disubstituted aromatic CH stretching band) band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.74 and 11.69 (2s, 1H, CONH); 8.12 5 and 7.92 (2s, 1H, N=CH); 7.78 (d, J: 1.8 Hz, 1H, furan C5-H); 7.64-7.60 (m, 2H, FPhC2,6-H); 7.50-7.45 (m, 2H, FPhC3,5-H); 7.01 and 6.99 (2s, 2H, aromatic C2,6- H); 6.54 (dd, J: 3.5, 1.8 Hz, 1H, furan C4-H); 6.24 (d, J: 3.5 Hz, 1H, furan C3-H); 4.46 and 4.08 (2s, 2H, SCH2); 3.81 and 3.83 (2s, 6H, Ph3,5-OCH3); 3.69 and 3.71 (2s, 3H, Ph4-OCH3) 10 - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.93 and 163.66 (C=O), 163.20 (d, J: 248.11 Hz), 153.61, 151.72, 147.85, 147.63 and 144.13 (C=N), 145.31, 141.36, 139.59, 130.68 (d, J: 9.18 Hz), 130.13 (d, J: 3.05 Hz), 129.92, 117.43 (d, J: 23.5 Hz), 112.12, 111.77, 104.65, 60.57, 56.36, 35.63 and 35.16 - ESI-HRMS: mass: m / z 511.1325, calculated [M+H]+: m / z 512.1403, found 15 [M+H]+: m / z 512.1415, calculated [MH]+: m / z 510.1247, found [MH]+: m / z Calculated for 510.1263; C24H22FN5O5S.0.5H2O: 55.38%C 4.45%H 13.45%N, Found: 55.21%C 4.683%H 13.25%N. 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-nitrophenyl) 20 [methylidene]acetohydrazide (Formula 2h) In the aforementioned Formula 2a-t, when Rıı = , it is represented by Formula 2h. molecules are obtained. Formula 2h 24 It is synthesized as a light yellow powder with a yield of 60-95% and melting point. Its temperature is between 107-109°C. - FTIR ν (cm-1): 3155 (NH stretch band), 3026 (ar CH stretch band), 2971, 2877 (aldehyde CH asymmetric and symmetric stretching band), 1687 (amide C=O stretching 5 band), 1589 (hydrazone C=N stretching band), 1567 (NITRO structure belonging to NO asymmetric stretching band), 1509 (aromatic C=C stretching, amide II NH bending and C- N stretching combination bands), 1453, 1340 (aldehyde CH asymmetric and symmetric 1340 (NITRO structure NO symmetrical stretch band), 1233 (C- S stretching band), 1185 (aromatic CF stretching band), 839 (1,4-disubstituted 10 aromatic CH stretch band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.97 (s, 1H, CONH); 8.27 (d, J: 8.9 Hz, 2H, aromaticC3,5-H); 8.11 (s, 1H, N=CH); 7.93 (d, J: 8.9, 2H, aromatic C2,6- H); 7.76 (d, J: 1.8 Hz, 1H, furan C5-H); 7.64–7.60 (m, 2H, FPhC2,6-H); 7.47 (t, J: 8.7 Hz, 2H, FPhC3,5-H); 6.53 (dd, J: 3.5, 1.8 Hz, 1H, furan C4-H); 6.22 (d, H: 3.5 15 Hz, 1H, furan C3-H); 4.5 and 4.11 (2s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 169.32 and 164.26 (C=O), 163.21 (d, J: 248.18 Hz), 151.76, 148.18, 147.88, 145.32, 145.19 and 142.05 (C=N), 141.31, 140.62, 130.66 (d, J: 9.15 Hz), 130.09 (d, J: 2.76 Hz), 128.23, 124.45, 117.48 (d, J: 23.56 Hz), 112.11, 111.82, 35.62 and 35.45 20 - ESI-HRMS: kütle: m / z 466.0859, hesaplanan [M+H]+: m / z 467.0937, month [M+H]+: m / z 467.0943, hesaplanan [MH]+: m / z 465.0781, moon [MH]+: m / z Calculated for 465.0796; C21H15FN6O4S.2H2O: 50.20%C 3.81%H 16.73%N, Found: 49.94%C 3.829%H 16.19%N. 30 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-methylphenyl) [methylidene]acetohydrazide (Formula 2i) In Formula 2a-t, when Rıı = , it is represented by Formula 2i. The molecule is obtained. 5 NN N HE F S HE NH N CH3 Formula 2i It is obtained as a white powder with a yield of 60-95% and its melting temperature is... It is in the range of 167-169.5°C. 10 - FTIR ν (cm-1): 3167 (NH stretch band), 3080 (ar CH stretch band), 2959, 2924 (aldehyde CH asymmetric and symmetric stretching band), 1671 (amide C=O stretching band) 1617 (hydrazone C=N stretching band), 1508 (aromatic C=C stretching, amide II NH bending and CN stretching combination bands), 1429, 1382 (aldehyde CH asymmetric and symmetric stretch band), 1222 (CS stretch band), 1155 (aromatic 15 CF stretching band), 843 (1,4-disubstituted aromatic CH stretching band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.69 and 11.61 (s, 1H, CONH); 8.15 and 7.97 (s, 1H, N=CH); 7.77 (d, J: 1.8 Hz, 1H, furan C5-H); 7.63-7.59 (m, 2H, FPhC2,6-H); 7.55 (d, J: 8.07 Hz, 2H, aromatic C 2,6 -H); 7.47 (td, J: 8.7; 1.72 Hz, 2H, FPhC3,5-H); 7.24 (d, J: 8.07 Hz, 2H, aromatic C 3,5 -H); 6.53 (dd, J: 3.57, 20 1.71 Hz, 1H, furan C4-H); 6.22 (d, J: 3.57 Hz, 1H, furan C3-H); 4.46 and 4.06 (2s, 2H, SCH2), 2.33 (s, 3H, PhCH3) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.77 and 163.58 (C=O), 163.20 (d, J: 248.23 Hz), 151.96, 147.84, 147.67 and 144.48 (C=N), 145.32, 26 141.40, 140.28, 131.67, 130.70 (d, J: 9.19 Hz), 130.15 (d, J: 2.75 Hz), 129.89, 127.31, 117.45 (d, J: 23.46 Hz), 112.12, 111.77, 35.69 and 35.63, 21.49. - ESI-HRMS: mass: m / z 435.1165, calculated [M+H]+: m / z 436.1243, found [M+H]+: m / z 436.1249, calculated [MH]+: m / z 434.1087, found [MH]+: m / z Calculated for 434.1102; C22H18FN5O2S.H2O: 58.27%C 4.45%H 15.44%N, 5 Found: 57.98%C 4.228%H 15.09%N. 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4-dimethoxy [phenyl)methylidene]acetohydrazide (Formula 2j) In Formula 2a-t, when Rıı = , it is represented by Formula 2j. molecules are obtained. NN N HE F S HE NH N HE CH3 O CH3 Formula 2j It is synthesized as a white powder with a yield of 60-95% and melting point. Its temperature is in the range of 200-202.5°C. - FTIR ν (cm-1): 3168, 3108 (NH stretch band), 3082, 3029, 3003 (ar CH (stretch band), 2981, 2925, 2837 (aldehyde CH asymmetric and symmetric stretching (band), 1678 (amide C=O stretching band), 1598 (hydrazone C=N stretching band), 20 1509 (combination of aromatic C=C stretching, amide II NH bending and CN stretching) bands), 1462, 1435, 1385 (aldehyde CH asymmetric and symmetric stretch band), 1221 (CS stretching band), 1143 (aromatic CF stretching band), 844 (1,4- disubstituted aromatic CH stretching band) 27 - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.62 and 11.56 (2s, 1H, CONH); 8.11 ve 7.92 (s, 1H, N=CH); 7.77 (d, J: 1.8 Hz, 1H, furan C5-H); 7.63-7.59 (m, 2H, FPhC2,6-H); 7.49-7.45 (m, 2H, FPhC3,5-H); 7.30 (d, 1H, J: 1.94 Hz, aromatikC2- H); 7.22 (dd, 1H, J: 8.31; 1.94 Hz, aromatikC6-H); 7.02 (d, 1H, J: 8.31 Hz, 5 aromatikC5-H); 6.53 (dd, J: 3.5, 1.8 Hz, 1H, furan C4-H); 6.22 (d, J: 3.5 Hz, 1H, furan C3-H); 4.45 ve 4.05 (2s, 2H, SCH2), 3.8 (s, 3H, Ph-3OCH3); 3.79 (s, 3H, Ph-4OCH3) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.70 ve 163.40 (C=O), 163.20 (d, J: 248.12 Hz), 151.72, 151.05, 149.43, 147.84, 147.79 ve 144.36 (C=N), 145.32, 141.39, 130.71 (d, J: 9.18 Hz), 130.15 (d, J: 3.24 Hz), 127.11, 121.56, 117.45 (d, J: 22.99 Hz), 112.13, 111.98, 111.84, 109.21, 56,01, 55.89, 35.67 ve 35.35 15 - ESI-HRMS: kütle: m / z 481.1220, hesaplanan [M+H]+: m / z 482.1298, bulunan [M+H]+: m / z 482.1304, calculated [MH]+: m / z 480.1141, found [MH]+: m / z Calculated for 480.1159; C23H20FN5O4S: 57.37%C 4.19%H 14.54%N, Found: 57.21%C 4.370%H 14.53%N. 20 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-methoxy) [methylidene]acetohydrazide (Formula 2k) In Formula 2a-t, when Rıı = , Formula 2k represents 25. molecules are obtained. 28 Formula 2k It is synthesized as a white powder with a yield of 60-95% and melting point. Its temperature is in the range of 194-195.5 °C. 5 - FTIR ν (cm-1): 3105 (NH stretch band), 3078 (ar CH stretch band), 2966 (aldehyde CH asymmetric and symmetric stretching band), 1681 (amide C=O stretching 1666 (hydrazone C=N stretching band), 1602 (aromatic C=C stretching, amide) II NH bending and CN stretching combination bands), 1453, 1377 (aldehyde CH asymmetric and symmetric stretch band), 1221 (CS stretch band), 1173 (aromatic 10 CF stretching band), 831 (1,4-disubstituted aromatic CH stretching band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.54 and 11.47 (s, 1H, CONH); 8.05 and 7.87 (s, 1H, N=CH); 7.70 (d, J: 1.7 Hz, 1H, furan C5-H); 7.58-7.64 (m, 2H, FPhC2,6-H); 7.53 (d, J: 8.76 Hz, 2H, aromatic C2,6-H); 7.39 (t, J: 8.7 Hz, 2H, FPhC3,5-H); 6.92 (d, J: 8.76 Hz, 2H, aromatic C3,5-H); 6.46 (dd, J: 3.5, 1.7 Hz, 15 1H, furan C4-H); 6.14 (d, J: 3.5 Hz, 1H, furan C3-H); 4.37 and 3.97 (2s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.64 and 163.44 (C=O), 163.21 (d, J: 248.32 Hz), 161.21, 151.74, 147.84, 147.53 and 144.28 (C=N), 145.31, 141.40, 130.69 (d, J: 9.18 Hz), 130.15 (d, J: 2.74 Hz), 128.92, 126.95, 117.45 (d, J: 23.39 Hz), 114.76, 112.12, 111.77, 55.73, 35.70 and 35.66 20 - ESI-HRMS: mass: m / z 451.1114, calculated [M+H]+: m / z 452.1192, found [M+H]+: m / z 452.1174, calculated [MH]+: m / z 450.1036, found [MH]+: m / z Calculated for 450.1040; C22H18FN5O3S: 58.53%C 4.02%H 15.51%N, Found: 58.41%C 3.953%H 15.32%N. 29 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- [cyanophenyl]methylidene]acetohydrazide (Formula 2l) In Formula 2a-t, when Rıı = , Formula 2l is used. The molecule shown is obtained. 5 NN N HE F S HE NH N N Formula 2l It is synthesized as a white powder with a yield of 60-95% and a melting point of 10°C. Its temperature ranges from 232 to 234.5°C. - FTIR ν (cm-1): 3190 (NH stretch band), 3101, 3011 (ar CH stretch band), 2929, 2864 (aldehyde CH asymmetric and symmetric stretching band), 2221 (C≡N (stretch band), 1681 (amide C=O gb), 1575 (hydrazone C=N stretch band), 1508 (aromatic C=C stretching, amide II NH bending and CN stretching combination 15) bands), 1454, 1361 (aldehyde CH asymmetric and symmetric stretch band), 1227 (CS stretch band), 1153 (aromatic CF stretch band), 839 (1,4-disubstituted aromatic CH stretch band); - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 12.02 and 11.92 (2s, 1H, CONH); 8.26 and 8.05 (2s, 1H, N=CH); 7.88 (d, J=8.1 Hz, 2H, CN-PhC2,6-H); 7.85 (d, J: 8.1 20 Hz, 2H, CN-PhC3,5-H); 7.77 (d, J: 1.8 Hz, 1H, furan C5-H); 7.64-7.60 (m, 2H, FPhC2,6-H); 7.47 (t, J: 8.7 Hz, 2H, FPhC3,5-H); 6.53 (dd, J: 3.5, 1.8 Hz, 1H, furan C4-H); 6.24 (d, J: 3.5 Hz, 1H, furan C3-H); 4.50 and 4.12 (2s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 169.27 (C=O), 163.18 (d, J: 242.35 Hz), 151.78, 147.87, 145.64 and 142.42 (C=N), 145.33, 141.36, 138.81, 133.16, 130.68 (d, J: 9.23 Hz), 130.12 (d, J: 2.71 Hz), 127.89, 119.11, 117.47 5 (d, J: 23.02 Hz), 112.26, 112.12, 111.79, 35.63 and 35.51 - ESI-HRMS: mass: m / z 446.0961, calculated [M+H]+: m / z 447.1039, found [M+H]+: m / z 447.1043, calculated [MH]+: m / z 445.0883, found [MH]+: m / z Calculated for 445.0898; C22H15FN6O2S. 0.5H2O: 58.02%C 3.54%H 18.45%N, Found: 58.49%C 3.506%H 18.47%N. 10 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-hydroxyphenyl) [methylidene]acetohydrazide (Formula 2m) When Rıı = in Formula 2a-t, Formula 2m yields 15. The molecule shown is obtained. NN N HE F S HE NH N OH Formula 2m It is synthesized as a white powder with a yield of 60-95% and a melting point of 20°C. Its temperature ranges from 264.5 to 267°C. - FTIR ν (cm-1): 3202 (NH stretch band), 3064 (ar CH stretch band), 2883, 2804 (aldehyde CH asymmetric and symmetric stretching band), 1659 (amide C=O stretching band) 1603 (hydrazone C=N stretching band), 1509 (aromatic C=C stretching, amide) 31 II NH bending and CN stretching combination bands), 1451, 1377 (aldehyde CH asymmetric and symmetric stretch band), 1224 (CS stretch band), 1144 (aromatic CF stretching band), 849 (1,4-disubstituted aromatic CH stretching band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.55 ve 11.48 (2s, 1H, CONH); 9.93 (s, 1H, OH); 8.08 ve 7.91 (2s, 1H, N=CH); 7.77 (d, J: 1.7 Hz, 1H, furan C5-H); 5 7.64-7.60 (m, 2H, FPhC2,6-H); 7.53 (d, J: 8.62 Hz, 2H, OH-PhC2,6-H); 7.48-7.45 (m, 2H, FPhC3,5-H); 6.82 (d, 2H, J: 8.62 Hz, OH-PhC3,5-H); 6.53 (dd, J: 3.5; 1.8 Hz, 1H, furan C4-H); 6.24 (d, J: 3.5 Hz, 1H, furan C3-H); 4.45 ve 4.05 (2s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.49 ve 163.28 (C=O), 10 163.2 (d, J: 248.57 Hz), 159.80, 151.73, 147.82, 147.94 ve 144,71 (C=N), 145.32, 141.38, 130.71 (d, J: 9.18 Hz), 130.14 (d, J: 3.15 Hz), 129.07, 125.38, 117.45 (d, J: 23.09 Hz), 116.17, 112.13, 111.78, 35.70 - ESI-HRMS: kütle: m / z 437.0957, hesaplanan [M+H]+: m / z 438.1036, bulunan [M+H]+: m / z 438.1038, hesaplanan [M-H]+: m / z 436.0879, bulunan [M-H]+: m / z 15 436.0895; C21H16FN5O3S. Calculated for 0.5 H2O: 56.5%C 3.84%H 15.69%N, Findings: 56.53%C 3.748%H 15.62%N. 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(3-hydroxyphenyl) [methylidene]acetohydrazide (Formula 2n) 20 In the aforementioned Formula 2a-t, when Rıı = , it is represented by Formula 2n. molecules are obtained. NN N HE F S HE NH N OH Formula 2n 25 32 It is synthesized as a white powder with a yield of 60-95% and melting point. Its temperature is 232-234.5°C. - FTIR ν (cm-1): 3157 (NH stretch band), 3073 (ar CH stretch band), 2962, 2830 (aldehyde CH asymmetric and symmetric stretching band), 1666 (amide C=O stretching band) band), 1612 (hydrazone C=N stretching band), 1510 (aromatic C=C stretching, amide 5 II NH bending and CN stretching combination bands), 1440, 1383 (aldehyde CH asymmetric and symmetric stretch band) 1225 (CS stretch band), 1155 (aromatic CF stretching band), 841 (1,4-disubstituted aromatic CH stretching band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.64 (s, 1H, CONH); 9.65 (2h, 1H, OH); 8.09 and 7.93 (2s, 1H, N=CH); 7.77 (d, J: 1.65 Hz, 1H, furan C5-H); 7.63-10 7.61 (m, 2H, FPhC2,6-H); 7.47 (t, J: 8.7 Hz, 2H, FPhC3,5-H); 7.24 (t, J: 7.81 Hz, aromatic C6-H); 7.16 (s, 1H, aromatic C2-H); 7.08 (d, J: 7.81 Hz, 1H, aromatic C5-H); 6.82 (d, J: 7.81 Hz, 1H, aromatic C4-H); 6.53 (dd, J: 3.53; 1.65 Hz, 1H, furan C4-H); 6.24 (d, J: 3.53 Hz, 1H, furan C3-H); 4.49 and 4.06 (2s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.79 and 163.69 (C=O), 15 163.22 (d, J: 248.72 Hz), 158.13, 151.73, 147.83, 147.73 and 144.69 (C=N), 145.30, 141.38, 135.60, 130.69 (d, J: 9.19 Hz), 130.35, 130.11 (d, J: 3.21 Hz), 119.00, 117.88, 117.47 (d, J: 23.40 Hz), 113.02, 112.12, 111.80, 35.71 - ESI-HRMS: mass: m / z 437.0957, calculated [M+H]+: m / z 438.1036, found [M+H]+: m / z 438.1039, calculated [MH]+: m / z 436.0879, found [MH]+: m / z 20 Calculated for 436.0895; C21H16FN5O3S: 57.66%C 3.69%H 16.01%N; Findings: 57.19%C 3.62%H 15.81%N. 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-chlorophenyl) [methylidene]acetohydrazide (Formula 20) 25 In Formula 2a-t, when Rıı = , Formula 2o The molecule shown is obtained. 33 Formula 2o It is synthesized as a white powder with a yield of 60-95% and melting point. Its temperature is in the range of 117-119°C. 5 - FTIR ν (cm-1): 3178 (NH stretch band), 3080 (ar CH stretch band), 2954 (aldehyde CH asymmetric and symmetric stretching band), 1672 (amide C=O stretching 1615 (hydrazone C=N stretching band), 1509 (aromatic C=C stretching, amide II NH bending and CN stretching combination bands), 1448, 1382 (aldehyde CH asymmetric and symmetric stretch band), 1223 (CS stretch band), 1125 (aromatic 10 CF stretching band), 843 (1,4-disubstituted aromatic CH stretching band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.82 and 11.74 (2s, 1H, CONH); 8.20 and 8.01 (2s, 1H, N=CH); 7.77 (m, 1H, furan C5-H); 7.73 (d, J: 8.59 Hz, 2H, ClPhC2,6-H), 7.63-7.60 (m, 2H, FPhC2,6-H), 7.52-7.45 (m, 4H, FPhC3,5-H and ClPhC3,5-H); 6.53 (m, 1H, furan C4-H); 6.24 (d, J: 3.58 Hz, 1H, furan C3-H); 4.47 15 and 4.08 (2s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.97 and 163.85 (C=O), 163.21 (d, J: 248.18 Hz), 151.89, 147.85, 146.34 and 143.13 (C=N), 145.32, 141.36, 134.92, 133.30, 130.68 (d, J: 9.22 Hz), 130.12 (d, J: 3.22 Hz), 129.35, 128.95, 117.46 (d, J: 23.30 Hz), 112.12, 111.80, 35.65 and 35.58 20 - ESI-HRMS: mass: m / z 455.0619, calculated [M+H]+: m / z 456.0697, found [M+H]+: m / z 456.0703, calculated [MH]+: m / z 454.0540, found [MH]+: m / z Calculated for 454.0557; C21H15ClFN5O2S.1H2O: 53.22%C 3.62%H 14.78%N, Found: 52.9%C 3.631%H 14.53%N. 34 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-fluorophenyl) [methylidene]acetohydrazide (Formula 2p) In the aforementioned Formula 2a-t, when Rıı = , it is represented by Formula 2p. The molecule is obtained. 5 NN N HE F S HE NH N F Formula 2p It is synthesized as a white powder with a yield of 60-95% and melting point. Its temperature is in the range of 129-131°C. 10 - FTIR ν (cm-1): 3180 (NH stretch band), 3078 (ar CH stretch band), 2964 (aldehyde CH asymmetric and symmetric stretching band), 1671 (amide C=O stretching band),1600 (hydrazone C=N stretching band), 1509 (aromatic C=C stretching, amide II NH bending and CN stretching combination bands), 1427, 1383 (aldehyde CH asymmetric and symmetric stretch band), 1232 (CS stretch band), 1155 (aromatic 15 CF stretching band), 839 (1,4-disubstituted aromatic CH stretching band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.7 (2s, 1H, CONH); 8.19 and 8.01 (2s, 1H, N=CH); 7.75–7.72 (m, 2H, N=C-FPhC2,6-H); 7.63–7.60 (m, 2H, FPhC2,6- H); 7.78 (m, 1H, furan C5-H); 7.47 (t, J: 8.74 Hz, 2H, FPhC3,5-H); 7.31–7.26 (m, 2H, N=C-FPhC3,5-H); 6.53 (dd, J: 3.57; 1.77 Hz, 1H, furan C4-H); 6.23 (d, J: 3.57 20 Hz, 1H, furan C3-H); 4.47 and 4.07 (2s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.90 and 163.75 (C=O), 163.50 (d, J: 247.76 Hz), 163.20 (d, J: 248.61 Hz), 151.70, 147.85, 146.52 and 143.25 (C=N), 145.32, 141.37, 130.99 (d, J: 2.78 Hz), 130.69 (d, J: 9.23 Hz), 130.13 (d, J: 3.23 Hz), 129.51 (d, J: 8.70 Hz), 117.46 (d, J: 23.54 Hz), 116.33 25 (d, J: 22.05 Hz), 112.12, 111.79, 35.65 and 35.59 35 - ESI-HRMS: kütle: m / z 439.0914, hesaplanan [M+H]+: m / z 440.0992, month [M+H]+: m / z 440.0976, calculated [MH]+: m / z 438.0836, found [MH]+: m / z 438.0840; C21H15F2N5O2S. Calculated for H2O: 55.14%C 3.75%H 15.31%N, Findings: 55.22%C 4.025%H 15.21%N. 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-bromophenyl) [methylidene]acetohydrazide (Formula 2r) In the aforementioned Formula 2a-t, when Rıı = , it is represented by Formula 2r. The molecule is obtained. 10 NN N HE F S HE NH N B r Formula 2r It is synthesized as a white powder with a yield of 60-95% and melting point. Its temperature is 120-122°C. 15 - FTIR ν (cm-1): 3178 (NH stretch band), 3079 (ar CH stretch band), 2961, 2925 (aldehyde CH asymmetric and symmetric stretching band), 1671 (amide C=O stretching band) 1615 (hydrazone C=N stretching band), 1509 (aromatic C=C stretching, amide II NH bending and CN stretching combination bands), 1447, 1381 (aldehyde CH asymmetric and symmetric stretch band), 1222 (CS stretch band), 1125 (aromatic 20 CF stretching band), 842 (1,4-disubstituted aromatic CH stretching band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.88 and 11.79 (2s, 1H, CONH); 8.23 and 8.04 (2s, 1H, N=CH); 7.83 (d, J: 1.67 Hz, 1H, furan C5-H); 7.71-7.65 (m, 6H, FPhC2,6-H and BrPhC2,3,5,6-H); 7.52 (t, J: 8.69 Hz, 2H, FPhC3,5-H); 6.58 (dd, J: 36 3.58; 1.67 Hz, 1H, furan C4-H); 6.29 (d, J: 3.58 Hz, 1H, furan C3-H); 4.52 and 4.13 (2s, 2H, SCH2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.97 and 163.86 (C=O), 163.20 (d, J: 248.78 Hz), 151.88, 147.85, 146.43 and 143.23 (C=N), 145.32, 141.35, 133.64, 132.27, 130.68 (d, J: 9.18 Hz), 130.11 (d, J: 2.76 Hz), 129.18, 5 123.70, 117.47 (d, J: 23.02 Hz), 112.12, 111.80, 35.66 and 35.58 - ESI-HRMS: mass: m / z 501.0239, calculated [M+H]+: m / z 502.0133, found [M+H]+: m / z 502.0178, calculated [MH]+: m / z 500.0161, found [MH]+: m / z Calculated for 0.5H2O: 500.0033; C21H15BrFN5O2S. 49.52%C 3.17%H 13.75%N, Found: 49.08%C 3.468%H 13.12%N. 10 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxyphenyl) [methylidene]acetohydrazide (Formula 2s) In the aforementioned Formula 2a-t, when Rıı = , it is represented by Formula 2s. The molecule is obtained. 15 NN N HE F S HE NH N OH Formula 2s It is synthesized as a white powder with a yield of 60-95% and melting point. Its temperature is in the range of 191-192.5°C. 20 - FTIR ν (cm-1): 3161 (NH stretch band), 3010 (ar CH stretch band), 2969, 2928, 2853 (aldehyde CH asymmetric and symmetric stretching band), 1672 (amide C=O (stretch band), 1617 (hydrazone C=N stretch band), 1511 (aromatic C=C (stress, amide II NH bending and CN strain combination bands), 1453, 1386 37 (aldehyde CH asymmetric and symmetric stretch band), 1225 (CS stretch band), 1154 (aromatic CF stretching band), 844 (1,4-disubstituted aromatic CH stretching band) band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.53 and 10.88 (2s, 1H, CONH); 10.01 (s, 1H, OH); 8.34 and 8.23 ​​(2s, 1H, N=CH); 7.69 (d, J: 1.7 Hz, 1H, furan C5-H); 5 7.57 (dd, 1H, J: 7.67; 1.5 Hz, OHPhC6-H); 7.55-7.52 (m, 2H, FPhC2,6-H); 7.39 (td, J: 8.7; 1.95 Hz, 2H, FPhC3.5-H); 7.22 (td, 1H, J: 7.67; 1.5 Hz, OHPhC4-H); 6.84 (d, 1H, J: 7.67 Hz, OHPhC3-H); 6.78 (t, 1H, J: 7.67 Hz, OHPhC5-H); 6.46 (dd, J: 3.6; 1.8 Hz, 1H, furan C4-H); 6.17 (d, J: 3.7 Hz, 1H, furan C3-H); 4.38 and 3.99 (2s, 2H, SCH2) 10 - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.55 and 163.62 (C=O), 163.25 (d, J: 248.75 Hz), 157.78, 151.65, 147.96, 147.83 and 141.95 (C=N), 145.36, 141.31, 131.98, 130.69 (d, J: 9.16 Hz), 130.13 (d, J: 2.79 Hz), 129.67, 119.83, 119.05, 117.49 (d, J: 23.01 Hz), 116.83, 112.14, 111.89, 35.71 and 35.37 - ESI-HRMS: mass: m / z 437.0957, calculated [M+H]+: m / z 438.1036, found 15 [M+H]+: m / z 438.1018, calculated [MH]+: m / z 436.0879, found [MH]+: m / z Calculated for 436.0883; C21H16FN5O3S: 57.66%C 3.69%H 16.01%N, Findings: 57.12%C 3.932%H 15.81%N. 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-dimethyl) [aminophenyl]methylidene]acetohydrazide (Formula 2t) 20 In Formula 2a-t, when Rıı = , it is represented by Formula 2t. molecules are obtained. NN N HE F S HE NH N N CH3 CH3 Formula 2t 38 It is synthesized as a white powder with a yield of 60-95% and melting point. Its temperature is in the range of 257-258.5°C. - FTIR ν (cm-1): 3161 (NH stretch band), 3074 (ar CH stretch band), 2895 (aldehyde CH asymmetric and symmetric stretching band), 1666 (amide C=O stretching 5 1607 (hydrazone C=N stretching band), 1510 (aromatic C=C stretching, amide II NH bending and CN stretching combination bands), 1445, 1384 (aldehyde CH asymmetric and symmetric stretch band) 1221 (CS stretch band), 1151 (aromatic CF stretching band), 844 (1,4-disubstituted aromatic CH stretching band) - 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.44 and 11.39 (2s, 1H, CONH); 8.03 10 and 7.87 (2s, 1H, N=CH); 7.78 (d, J: 1.7 Hz, 1H, furan C5-H); 7.63-7.59 (m, 2H, FPhC2,6-H); 7.51-7.44 (m, 6H, FPhC3,5-H and N(CH3)2PhC2,3,5,6-H); 6.54 (dd, J: 3.5; 1.7 Hz, 1H, furan C4-H); 6.24 (d, J: 3.5 Hz, 1H, furan C3-H); 4.43 and 4.03 (2s, 2H, SCH2), 2.97 (s, 6H, -N(CH3)2) - 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.26 and 162.97 (C=O), 15 163.20 (d, J: 248.36 Hz), 152.03, 151.88, 148.41 and 145.18 (C=N), 147.82, 145.32, 141.43, 130.71 (d, J: 9.23 Hz), 130.18 (d, J: 2.78 Hz), 128.62, 121.68, 117.45 (d, J: 22.96 Hz), 112.22, 112.13, 111.83, 40.20, 35.76 and 35.73 - ESI-HRMS: mass: m / z 464.1430, calculated [M+H]+: m / z 465.1509, found [M+H]+: m / z 465.1515, calculated [MH]+: m / z 463.1352, found [MH]+: m / z 20 Calculated for 463.1369; C23H21FN6O2S: 59.47%C 4.56%H 18.09%N, Found: 59.40%C4.771%H 18.04%N. The molecules that are the subject of the invention are 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- yl]sulfanyl]acetohydrazide (Formula 1) and 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazole-25 3-yl]sulfanyl]-N'-[(substituted phenyl)methylidene]acetohydrazide (Formula 2a) and its derivatives The synthesis steps for (Formula 2a-t) are Reaction i, Reaction ii, Reaction iii, Reaction i, respectively. Reaction iv is shown below, where v is the reaction. 39 One of the molecules involved in the invention is 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol- Synthesis method of 3-yl]sulfanil]acetohydrazide (Formula 1); i. 0.03 mol of furan-2-carbohydrazidine solution in absolute ethanol is mixed with 0.03 Addition of 4-fluorophenyl isothiocyanate and reversing in a water bath 5 Heating under a cooler for 1-4 hours, filtering the resulting precipitate after 1 day, and As a result of drying, N-(4-fluorophenyl)-2-(furan-2-carbonyl)hydrazine-1- Preparation of carbothioamide (Reaction i), ii. N-(4-fluorophenyl)-2-(furan-2-carbonyl)hydrazine-1-carbotioamide 2N 10 in sodium hydroxide (NaOH) under recirculating condenser for 2-4 hours heating and the resulting 4-(4-fluorophenyl)-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3- Precipitation of thion with 12.5% ​​hydrochloric acid (HCl) and subsequent precipitation Washing the product with distilled water and drying it results in 4-(4-Fluorophenyl)-5- Preparation of (furan-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-thion (Reaction II) iii. 0.005 mol 4-(4-fluorophenyl)-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-15 Preparation of thione suspension in ethanol and the aforementioned 0.005 mol potassium carbonate (K2CO3) and 0.0055 mol ethyl alcohol were added to the suspension. Addition of bromoacetate and 5-6 minutes under refrigerated cooling in a water bath. After heating for an hour, the reaction medium is poured into ice water and It is left in the refrigerator for 1 day, after which the precipitated ethyl ((4-20 filtering the fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl)sulfanyl)acetate and As a result of drying, ethyl ((4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- Preparation of (il)sulfanyl)acetate (Reaction iii), 40 iv. 0.005 mol ethyl ((4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazole-3- (i)sulfanil)acetate and 0.028 mol hydrazine hydrate reversible in ethanolic medium The subject of the invention, 2-[[4-(4-Fluorophenyl)-, is obtained by heating under a cooler for 5-6 hours. 5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanil]acetohydrazide molecule (Formula 1) Obtaining (Reaction iv) 5 It includes the processing steps. N-(4-fluorophenyl)-2-(furan-2-carbonyl)hydrazine-1- carbotioamide, 4-(4-Fluorophenyl)-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thion, ethyl ((4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl)sulfanyl)acetate and the subject of the invention 2-[[4-(4- Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide molecule (Formula 1) It is obtained with a yield of 60-95%. 10 The molecules that are the subject of the invention are 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- Synthesis of [il]sulfanil]-N'-[(substituted phenyl)methylidene]acetohydrazide derivatives (Formula 2a-t) method; i. 0.03 mol of furan-2-carbohydrazide solution in absolute ethanol is mixed with 0.03 mol of 4- Addition of fluorophenyl isothiocyanate and refluxing in a water bath 15 Heating it under water for 1-4 hours, filtering the resulting precipitate after 1 day, and As a result of drying, N-(4-fluorophenyl)-2-(furan-2-carbonyl)hydrazine-1- Preparation of carbothioamide (Reaction i), ii. N-(4-fluorophenyl)-2-(furan-2-carbonyl)hydrazine-1-carbotioamide 2N 20°C in sodium hydroxide (NaOH) under recirculating cooler for 1-4 hours heating and the resulting 4-(4-fluorophenyl)-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3- Precipitation of thion with 12.5% ​​hydrochloric acid (HCl) and subsequent precipitation Washing the product with distilled water and drying it results in 4-(4-Fluorophenyl)-5- Preparation of (furan-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-thion (Reaction II) iii. 0.005 mol 4-(4-fluorophenyl)-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-25 0.005 mol of potassium carbonate (K2CO3) was added to the suspension of thion in ethanol. Addition of 0.0055 mol ethyl bromoacetate and condensation in a water bath. After heating for 5-6 hours, the reaction contents are placed in ice water. poured and left in the refrigerator for 1 day, then it collapses. filtration of ethyl ((4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl)sulfanyl)acetate 30 and as a result of drying, ethyl ((4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- Preparation of (il)sulfanyl)acetate (Reaction iii), 41 iv. 0.005 mol ethyl ((4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazole-3- (i)sulfanil)acetate and 0.028 mol hydrazine hydrate reversible in ethanolic medium The subject of the invention, 2-[[4-(4-Fluorophenyl)-, is obtained by heating under a cooler for 5-6 hours. 5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanil]acetohydrazide molecule (Formula 1) Obtaining (Reaction iv), 5 v. 0.003 mol 2-[[4-(4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazole-3- 0.003 mol of [il]sulfanil]acetohydrazidine (Formula 1) solution in absolute ethanol addition of aromatic aldehyde compound and immersion of the reaction mixture in a water bath boiled under a refrigerating cooler for 5-6 hours and then... cooling, filtration of precipitated hydrazide-hydrazones, and mixing with boiling ethanol 10 As a result of purification by washing, the subject of the invention is 2-[[4-(4-Fluorophenyl)-5-(furan-2- yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(substituted phenyl)methylidene]acetohydrazide Preparation of derivatives (Formula 2a-t) in different reaction flasks It includes the processing steps. N-(4-fluorophenyl)-2-(furan-2-carbonyl)hydrazine-1- carbotioamide, 4-(4-Fluorophenyl)-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thion, ethyl 15 ((4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl)sulfanyl)acetate and 2-[[4-(4-Fluorophenyl)-5- (furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide molecule (Formula 1) 60-95% It is obtained with a yield of (1.1 g). Figure 1 shows the molecules that are the subject of the invention, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4- triazol-3-yl]sulfanyl]acetohydrazide (Formula 1) and 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-2O 1,2,4-triazol-3-yl]sulfanyl]-N'-[(substituted phenyl)methylidene]acetohydrazide derivatives (Formula 2a-t) and the 24-hour standard combination of cisplatin and osimertinib. Comparative study showing the effect of the application on the viability of MCF-7 cells. A bar graph is included. In other words, looking at Figure 1, the subject of the invention is shown. molecules that have an effect similar to standard drugs on MCF-7 breast cancer cell lines 25 It appears to exhibit a certain level of inhibition. Figure 2 shows the molecules that are the subject of the invention: 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4- triazol-3-yl]sulfanyl]acetohydrazide (Formula 1) and 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 30 derivatives of 1,2,4-triazol-3-yl]sulfanil]-N'-[(substituted phenyl)methylidene]acetohydrazide (Formula 2a-t) and the standard substances cisplatin and osimertinib 24 demonstrating the effect of hourly application on the viability of HEK293 cells 42 A comparative bar graph is included. Figure 2 shows the molecules subject to the invention, HEK293. while on healthy cell lines at higher concentrations than standard drugs They exhibit toxic effects. In other words, the potential side effects of the molecules that are the subject of this invention. It is less common than standard medications. The molecules that are the subject of the invention are 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-5 in Figure 3-101. triazol-3-yl]sulfanyl]acetohydrazide (Formula 1) and 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(substituted phenyl)methylidene]acetohydrazide derivatives (Formula 2a-t) FTIR, 1H-NMR and ESI-HRMS (negative and positive) spectra. It is shown. Table 1. Molecules of the invention: 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol- 3-yl]sulfanyl]acetohydrazide (Formula 1) and 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4- [triazol-3-yl]sulfanil]-N'-[(substituted phenyl)methylidene]acetohydrazide derivatives (Formula 2a- t) and cisplatin and osimertinib, which are used as standard substances, according to MCF-7 and HEK293 IC50 values ​​on the cells. 15 IC50 IC50 HEK293 MCF-7 HEK293 MCF-7 Formula 1 >50 25.41 ± 0.93 Formula 2j 44.56 ± 1.02 >50 Formula 2a >50 35.17 ± 1.29 Formula 2k 39.18 ± 1.07 44.25 ± 1.08 Formula 2b 42.01 ± 0.92 34.21 ± 0.65 Formula 2l >50 33.57 ± 1.78 Formula 2c 45.32 ± 1.15 >50 Formula 2m 26.13 ± 0.87 29.13 ± 0.77 Formula 2d >50 40.45 ± 0.85 Formula 2n 32.78 ± 0.56 26.17 ± 1.29 Formula 2e 43.05 ± 1.13 35.12 ± 1.60 Formula 2o 36.16 ± 0.75 27.22 ± 0.55 Formula 2f >50 >50 Formula 2p 31.55 ± 1.07 20.35 ± 0.65 Formula 2g >50 46.08 ± 1.11 Formula 2r 37.19 ± 0.77 21.98 ± 1.04 Formula 2h >50 43.54 ± 0.96 Formula 2s 39.87 ± 1.06 23.15 ± 0.66 Formula 2i 37.18 ± 0.77 31.74 ± 1.16 Formula 2t 43.14 ± 1.45 31.15 ± 1.11 Osimertinib 2.98  0.05 10.11  0.22 Cisplatin 10.17  1.39 08.13  0.45 As can be clearly seen from Table 1, these are highly effective molecules on the market. The lethal effect of cisplatin and osimertinib molecules on normal cells. While their lethal effects are higher, the toxicity of the molecules that are the subject of the invention is 20. It is quite small compared to molecules, in other words, the possible values ​​of the molecules that are the subject of the discovery. Its side effects are much lower compared to cisplatin and osimertinib molecules. 43 Table 2. Molecules of the invention: 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol- 3-yl]sulfanyl]acetohydrazide (Formula 1) and 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4- [triazol-3-yl]sulfanil]-N'-[(substituted phenyl)methylidene]acetohydrazide derivatives (Formula 2a- t) Inhibitory activities on the cyclooxygenase enzymes COX-1 and COX-2. % inhibition (20 uM) % inhibition (20 µM) COX-1 COX-2 COX-1 COX-2 Formula 1 48.67 ± 0.94 71.32 ± 1.05 Formula 2j 55.17 ± 1.04 69.87 ± 0.18 Formula 2a 35.12 ± 0.85 69.18 ± 0.12 Formula 2k 53.59 ± 1.83 72.93 ± 1.39 Formula 2b 49.14 ± 0.87 63.73 ± 0.98 Formula 2l 65.71  0.59 75.04  0.49 Formula 2c 37.55 ± 1.34 62.66 ± 0.98 Formula 2m 55.90 ± 1.03 59.39 ± 0.84 Formula 2d 48.02 ± 0.94 70.32 ± 1.03 Formula 2n 55.19 ± 0.78 67.39 ± 1.38 Formula 2e 35.12  1.04 63.93 ± 0.82 Formula 2o 45.37 ± 0.93 77.18 ± 0.25 Formula 2f 42.14 ± 0.87 59.73 ± 1.12 Formula 2p 39.93 ± 1.58 79.03 ± 0.48 Formula 2g 37.55 ± 1.34 62.66 ± 0.98 Formula 2r 41.64 ± 1.62 82.36 ± 1.29 Formula 2h 42.14 ± 0.87 59.73 ± 1.12 Formula 2s 33.89 ± 0.81 85.26 ± 1.84 Formula 2i 37.55 ± 1.34 62.66 ± 0.98 Formula 2t 40.15 ± 1.54 82.27 ± 0.79 Diclofenac 99.97 ± 0.77 99.98 ± 0.25 Celecoxib 99.85  0.85 99.91  1.03 Ibuprofen 99.79 ± 0.35 99.09 ± 0.46 SC-560 99.98  1.07 99.86  0.92 Dup-697 99.78 ± 0.94 99.95 ± 0.36 As clearly shown in Table 2, the molecules subject to the invention are commercially available. It exhibits effects similar to / close to molecules whose selectivity and efficacy have been proven. Table 3. Cyclooxygenase (COX) IC50 values ​​of the active ingredients. 44 Item No. IC50 SI COX-1 COX-2 Formula 2r ND 16.05 ± 1.03 (µM) ND Formula 2s 51.15  1.29 (µM) 10.21  0.57 (µM) 0.19 Formula 2t 33.91  1.92 (µM) 15.18  0.75 (µM) 0.44 Diclofenac 56.16  0.07 (nM) 35.05  0.18 (nM) 0.62 Ibuprofen 12.37  1.05 (µM) 85.20  5.20 (µM) 6.88 Celecoxib 9.15  1.05 (µM) 1.03  0.02 (µM) 0.11 SC-560 10.17  1.15 (nM) 5.98  0.46 (µM) >50 Dup-697 9.5  0.12 (µM) 70.44  0.12 (nM) 0.007 The molecules that are the subject of the invention are 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- [1]sulfanil]acetohydrazidine (Formula 1) and 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4- [triazol-3-yl]sulfanil]-N'-[(substituted phenyl)methylidene]acetohydrazide derivatives (Formula 2a- t) Analysis of the effects on the MCF-7 breast cancer cell line in humans 5 Some studies have been carried out to enable this. HEK293 and used in the experiments. For MCF-7 cell line amplification, "Dulbecco's modified Eagle medium / High" was used. Glucose” (DMEM / High, Gibco 41966) was used. DMEM / high glucose content It contains pyruvate, L-glutamine, and 4.5 g / L D-glucose. It will be used in experiments. Culture medium; sterile medium solution containing 10% (v / v) fetal bovine serum (FBS, Gibco), and 1% 10% It was prepared by adding (v / v) antibiotic-antifungal solution (Gibco). Additionally... The cells were obtained from ATCC. After cell opening, the cell culture flask was used. It was transferred to an incubator at 37°C. Cell culture was started 24 hours after the cells were thawed. The viability of the cells in the flask is checked according to their adhesion status using an inverted microscope. This has been done. When the cells multiply to the point where they cover 80 percent of the surface, then 15 Passage procedures have been completed. In the process of preparing cell subcultures, first a 25 cm2 cell culture medium is prepared. The culture medium in the container was removed and 5 ml of "Dulbecco Phosphate Buffered Saline Solution" was added. It was washed with (D-PBS). After the washing process, the D-PBS was removed from the environment. Add 1 mL of Trypsin / EDTA to help the cells lift off the surface of the culture dish. The culture dish was placed in an incubator and the cells were separated from the surface and from each other. To make the separation, gently and physically tap the edge of the culture dish by hand. The process has been completed. The cells have completely lifted from the surface of the culture dish; then invert. This was checked under a microscope. After the separation process was complete, trypsin activity was measured. To terminate, 5 ml of culture medium was placed in a culture dish and pipetted. Cell 25 45 The count was performed using a hemocytometer (Neubauer slide). The cells were transferred to a new culture dish. It was placed in and then topped up to 7 ml with fresh culture medium. The cells were over 90%. a 37°C incubator providing relative humidity and 5% CO2 (Thermo Scientific, Heracell™ 150i) removed and this procedure is done two or three times a week for cell continuity. The process was repeated. Subculture of the cells was performed in a sterile environment with laminar airflow. 5 This was performed in the cabin (Heal Force HFsafe-1200 version 2.01). After preparing subcultures of HEK293 and MCF-7 cells, the subject of the invention molecules 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- [1]sulfanil]acetohydrazidine (Formula 1) and 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4- [triazol-3-yl]sulfanil]-N'-[(substituted phenyl)methylidene]acetohydrazide derivatives (Formula 2a-10 t) Cytotoxicity analyses were also performed. In this method, firstly, live organisms were analyzed. Thanks to the activity of mitochondrial dehydrogenase enzyme in cells, MTT [3-(4,5- The tetrazolium ring of the dimethylthiazol-2,5-diphenyltetrazolium molecule has been cleaved and The MTT molecule has been successfully converted into water-insoluble formazan crystals. After the resulting formazan crystals are dissolved with the help of dimethyl sulfoxide (DMSO), 15 Then absorbance measurement was performed using a spectrophorometer. For cytotoxicity analysis. The following steps were carried out in sequence. First, a 96-well culture was created. 200 µl of cell suspension (5.104 cells / well) was added to each well of the containers. The culture dish was placed in an incubator at 37ºC providing 5% carbon dioxide (CO2). It was done. The culture medium on the cells adhering to the surface of the wells, 24. 20 It was removed at the end of the hour. First, culture media containing 50 µM of substance. Their viability was analyzed, and then their effects at different concentrations were also tested. The experimental group cells were coated with culture media containing different concentrations of agents. The control group received only 200 µl of culture medium (DMEM / High, Gibco 41966). applied and kept in an incubator (37ºC, 5% CO2) and the 24-hour incubation period was 25 Finally, the culture medium covering the cells was removed. Then, 30 µl of MTT was added. Stock solution (5mg / ml, prepared in PBS) was added and left for 4 hours. It was kept in an incubator. 150 µl of isopropanol was used to dissolve the formazan crystals. The culture dish was added and shaken at room temperature to ensure solution homogeneity. (Heidolph Unimax 1010) was shaken. In the next step, the resulting colored product was 570 30 The absorbance at nm wavelength was measured using a microplate reader (Spektramax i3) and The results were evaluated according to the following equation. Experiments were conducted three times each. It was performed repeatedly and in three separate periods. 46 To be able to test the COX-1 and COX-2 enzyme activities of the synthesized molecules. For this purpose, the substances were dissolved in DMSO, and then the effect of DMSO was observed. eliminated and DMSO ratio in the solutions from the buffer included in the kit The concentration was reduced to below 1% with the solution. The synthesized substances reduced COX-1 (sheep 5 It was tested whether it inhibited COX-2 (human recombinant) and COX-2 (human recombinant). In the experiment, the reaction between PGG2 and 10-acetyl-3,7-dihydroxyphenoxazine (ADHP), It produces resorufin, a highly fluorescent compound. The result of the experiment... Fluorescence was measured and % inhibition values ​​were calculated. Enzyme inhibition assay, kit. (COX Fluorescent Inhibitor Screening Assay Kit (Cayman, 700100)) manufacturer's 10 carried out in accordance with the instructions and enzyme inhibition of the substances In the multimode microplate reader (Spektramax i3), an excitation wavelength of 530-540 nm is used. The wavelength was measured with an emission wavelength of 585-595 nm. The substances were 10 µM. Enzyme inhibitions at certain concentrations were compared to standards. It has been evaluated. 15 All experiments were conducted at three different times and repeated at least three times. Statistical data is based on GraphPad Prism software version 7.02 (La Jolla, California, USA). The differences between the groups were evaluated using one-way analysis of variance. (ANOVA) was evaluated using Dunnet's multiple comparison test. (at least P< 0.05). 20 The effects of the agents used in the study on MCF-7 and HEK293 cells Viability tests to determine cytotoxic effects are performed in 3x3 replicates. This was carried out. The control group in the experiments was the group that did not receive any agent. It was determined as such and considered to be 100% alive. Within the experimental groups One-way ANOVA (one-25) was used to analyze the consistency between the obtained data. A 100-degree ANOVA test was applied. The significance of the groups compared to the control group was determined. The agents were evaluated using the Dunnett test and the Tukey test. Literature reviews revealed the following: Application concentrations and timing were determined. Applied to the cells. The concentration values ​​(IC50) at which the agents reduce cell viability by half have been calculated. 47 Sigmoidal dose-response curve (sigmoidal dose) for calculating the IC50 value of agents. The response variable (slope) was calculated using GraphPad Prism® 7.0 software. The aim is to determine the cytotoxic effects of substances on MCF-7 and HEK293 cells. cultures containing different concentrations (50-0.1 µM) of substances were added to 24-hour cultures. Culture media were added. The control group, which received no substance, also had culture media 5. The data were refreshed and then the MTT test was performed after a 24-hour incubation period. The viability results of experiments with 50 µM substance applied are shown in Figure 1 and... This is shown in Figure 2. The IC50 results for the substances are shown in Table 1. Testing the inhibitory effects of the molecules described in the invention on COX-1 and COX-2 enzymes. To achieve this, the procedures recommended by the manufacturer were followed. For this purpose, 10 First, the substances were incubated with enzymes, then 20 µM 200 µl of the substance-enzyme cocktail containing the substance was placed in 96-well plates. Enzyme activity was measured for each substance in triplicate and at three different time points. This was carried out by analyzing the consistency between replicates of the experimental groups. A one-way ANOVA test was applied. The groups were given a standard 15-degree scale. inhibitors (SC-560 for COX-1, DuP-697 for COX-2, celecoxib and indomethacin) The significance of the substances according to their group was evaluated using the Dunnett test. The substances were at 20 µM. COX-1 and COX-2 enzyme inhibitions at different concentrations are shown in Table 2, along with their IC50 values. The results are shown in Table 3. All values ​​are statistically significant. This shows (at least P<0.05). 20 30 48 References [1] Visser KE, Eichten A, Coussens LM. Paradoxical roles of the ımmune system during cancer development. Nat Rev Cancer 2006; 6: 24-37. [2] Aggarwal BB, Shishodia S, Sandur SK, Pandey MK, Sethi G. Inflammation and 5 cancer: How hot is the link?. Biochem Pharmacol 2006; 72: 1605-21. [3] Medzhitov R. Inflammation: New adventures of an old flame. Cell 2010; 140: 771- 76. [4] Čalija, B. (Ed.). (2017). Microsized and nanosized carriers for nonsteroidal anti- inflammatory drugs: formulation challenges and potential benefits. Academic Press. 10 [5] Atmaca, S. (2019). Meme Kanserı̇ Hücre Dı̇zı̇sı̇ Üzerı̇nde (Mcf-7), Bı̇sdemethoxycurcumı̇n Ve Methotrexate’In Antı̇prolı̇feratı̇f Ve Apopı̇totı̇k Etkı̇lerı̇nı̇n Araştirilmasi (thesis). [6] SAMELIUK, Y. G., Zedan, F. A., & Kaplaushenko, T. M. (2021). 1,2,4-TRIAZOLE DERIVATIVES IN MEDICINE AND PHARMACY AND APPLICATION PROSPECTS. 15 Ukraine. Retrieved from https: / / dergipark.org.tr / en / download / article-file / 1598512.

Claims

49 REQUESTS 1. Formula X indicates the MCF-7 breast cancer cell line and cyclooxygenase 1. (COX-1) has an effect on and especially on the cyclooxygenase-2 (COX-2) isoenzyme. Triazoles and 5 that exhibit selective inhibitory properties and have antitumoral effects. It is a hydrazide-hydrazone derivative molecule, Formula X Here, R is selected from the following formulas; Ri= -HN NH2 , 10 2. If Rı = -HN NH2, then according to Claim 1, shown by Formula 1, one molecule. Formula 1 3. According to claim 2, it is a molecule and its characteristic is; the molecule is 2-[[4-(4-Fluorophenyl)-5-(furan-15 [2-yl)-4H-1,2,4-triazol-3-yl]sulfanil]acetohydrazide (Formula 1). Ri 50 4. A molecule according to either claim 2 or 3, and its property is; 2-[[4-(4- Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide molecule (Formula 1) states that the melting point is 166-168°C.

5. A molecule according to either claim 2 or 3, and its property is; 2-[[4-(4- 5 of the fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide molecule (Formula 1) Fourier Transform Infrared Spectroscopy (FTIR) spectrum, (FTIR) ν (cm-1): 3317, 3257 cm-1 (NH voltage band); 3152, 3043 cm-1 Aromatic CH tension band; asymmetric aldehyde CH at 2900, 2850 cm-1. Symmetric, voltage band C=O at 1679 cm-1; hydrazone voltage band C=N at 1610 cm-1. band, aromatic C=C stretching band at 1506 cm-1, amide II NH bending and CN 10 strain combination bands); asymmetric aldehyde CH at 1429, 1398 cm-1 and symmetrical stretch band); CS stretch band at 1215 cm-1, aromatic at 1205 cm-1 CF stretching band) and 1,4-disubstituted aromatic CH stretching band at 837 cm-1 It includes its peaks.

6. A molecule according to either claim 2 or 3, and its property is; 2-[[4-(4-15 Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide molecule (Formula 1) 1H-NMR spectrum, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 9.37 (s, 1H, CONH); 7.77 (d, J: 1.6 Hz, 1H, furan C5-H); 7.63-7.59 (m, 2H, FPhC2,6-H); 7.47 (t, J: 8.65 Hz, 2H, FPhC3.5-H); 6.54 (dd, J: 3.5; 1.6 Hz, 1H, furan C4-H); 6.24 (d, J: 3.5 Hz, 1H, furan C3-H); 4.32 (s, 2H, NH2) and 3.88 (s, 20 It contains 2H, SCH2) peaks.

7. A molecule according to either claim 2 or 3, and its property is; 2-[[4-(4- Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide molecule (Formula 1) 13C-NMR spectrum, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 166.43, 163.22 (d, J: 252 Hz), 151.8, 148.01, 145.34, 141.40, 130.71 (d, 25 J: 9.5 Hz), 130.06 (d, J: 3 Hz), 117.47 (d, J: 22 Hz), 112.15, 111.8 and 34.9 It includes its peaks.

8. A molecule according to either claim 2 or 3, and its property is; 2-[[4-(4- Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide molecule (Formula 1) electrospray ionization mass spectrum, ESI-HRMS: [M+H]+: 30 It includes peaks m / z 422.1091 and [MH]+: m / z 420.0946.

9. A molecule according to either claim 2 or 3, and its property is; 2-[[4-(4- Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide molecule (Formula 1) The molecular weight is 333.0695 g / mol. 51 10. A molecule according to either claim 2 or 3, and its property is; 2-[[4-(4- Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide molecule (Formula 1) contains 58.17% C, 3.909% H, and 15.79% N by mass.

11. According to claim 1, a molecule has the property that; when R = The molecule in question is represented by the formula 2a-t. 5 Formula 2a-t And Rıı is selected from the following formulas. -H Formula a Formula b Formula c Formula d 10 Formula e Formula f Formula g 52 Formula h Formula i Formula j Formula k Formula l Formula m Formula n Formula o Formula p Formula r Formula s Formula t 12. A molecule according to Claim 11 that has any of the following formulas; 10  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'- [(phenyl)methylidene]acetohydrazide (Formula 2a)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,3- [dihydroxyphenyl)methylidene]acetohydrazide (Formula 2b)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-4-15 [diethylaminophenyl]methylidene]acetohydrazide (Formula 2c)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-3- [methoxyphenyl]methylidene]acetohydrazide (Formula 2d) 53  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- [ethylphenyl]methylidene]acetohydrazide (Formula 2e)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,4- [Dinitrophenyl]methylidene]acetohydrazide (Formula 2f)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4,5-5 trimethoxyphenyl)methyldene]acetohydrazide (Formula 2g)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- nitrophenyl)methyldene]acetohydrazide (Formula 2x)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- methylphenyl)methylidene]acetohydrazide (Formula 2i) 10  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4- dimethoxyphenyl)methyldene]acetohydrazide (Formula 2h)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- methoxy)methyldene]acetohydrazide (Formula 2k)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-15 cyanophenyl)methyldene]acetohydrazide (Formula 2l)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- [hydroxyphenyl]methylidene]acetohydrazide (Formula 2m)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(3- [hydroxyphenyl)methylidene]acetohydrazide (Formula 2n) 20  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- [chlorphenyl]methylidene]acetohydrazide (Formula 2o)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- [florphenyl)methylidene]acetohydrazide (Formula 2p)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-25 [bromphenyl)methylidene]acetohydrazide (Formula 2r)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2- [hydroxyphenyl)methylidene]acetohydrazide (Formula 2s)  2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4- [dimethylaminophenyl]methylidene]acetohydrazide (Formula 2t) 30 13. A molecule according to claim 11 or 12, whose property is; R1 as "Formula a" If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- 54 Obtaining the molecule [il]sulfanil]-N'-[(phenyl)methylidene]acetohydrazide (Formula 2a) It is done.

14. According to claim 13, it is a molecule with the property of 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(phenyl)methylidene]acetohydrazide molecule (Formula 2a) The melting point is 119-121°C. 5 15. According to claim 13, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(phenyl)methylidene]acetohydrazide molecule (Formula 2a) FTIR spectrum, FTIR ν (cm-1): 3419 cm-1 NH stretching band, 3177, 3086 cm-1 aromatic CH stretching band, 2964 cm-1 aldehyde CH asymmetric and symmetrical stretching band, 1670 cm-1 amide C=O stretching band, 1600 cm-1 hydrazone 10 C=N stretching band, 1509 cm-1 aromatic C=C stretching band, amide II NH bending and CN stretching combination bands, 1403, 1383 cm-1 aldehyde CH asymmetric and symmetrical stretch band, 1223 cm⁻¹ CS stretch band, 1202 cm⁻¹ aromatic CF stretching band and 841 cm-1 1,4-disubstituted aromatic CH stretching band peaks It includes. 15 16. According to claim 13, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(phenyl)methylidene]acetohydrazide molecule (Formula 2a) 1H-NMR spectrum, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.73 and 11.68 (2s, 1H, CONH); 8.19 and 8.01 (2s, 1H, N=CH); 7.77 (d, J: 1.8 Hz, 1H, furan C5-H); 7.49-7.42 (m, 9H, aromatic CH); 6.53 (dd, J: 3.4; 1.8 Hz, 1H, furan 20 C4-H); 6.23 (d, J: 3.4 Hz, 1H, furan C3-H); 4.48 and 4.07 (2s, 2H, SCH2) peaks It includes.

17. According to claim 13, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(phenyl)methylidene]acetohydrazide molecule (Formula 2a) 13C-NMR spectrum, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 25 168.90 and 163.74 (C=O); 163.21 (d, J: 248 H); 151.95; 147.85; 147.65 and 144.41 (C=N); 145.32; 141.38; 134.36; 130.69 (d, J: 9.17 Hz); 130.47; 130.13 (d, J: 3 Hz); 129.28; 127.33; 117.46 (d, J: 23 Hz); 112.13; 111.80; 35.68 and 35.61 It includes its peaks.

18. According to claim 13, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-30 1,2,4-triazol-3-yl]sulfanil]-N'-[(phenyl)methylidene]acetohydrazide molecule (Formula 2a) Mass spectrum of electrospray ionization, ESI-HRMS: [M+H]+: m / z It includes the peaks 422.1091 and [MH]+: m / z 420.0930. 55 19. According to claim 13, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(phenyl)methylidene]acetohydrazide molecule (Formula 2a) It contains 58.17% C, 3.909% H, and 15.79% N by mass.

20. According to claim 13, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(phenyl)methylidene]acetohydrazide molecule (Formula 5 2a) its molecular weight is 421.1008 g / mol.

21. A molecule according to claim 11 or 12, whose property is; R1 as "Formula b". If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- [il]sulfanil]-N'-[(2,3-dihydroxyphenyl)methylidene]acetohydrazidine (Formula 2b) is obtained. It is done. 10 22. According to claim 21, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,3-dihydroxyphenyl)methylidene]acetohydrazidine (Formula 2b) states that the melting point is 190-192.5°C.

23. According to claim 21, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,3-dihydroxyphenyl)methylidene]acetohydrazide 15 The FTIR spectrum of the molecule (Formula 2b) has an FTIR ν (cm-1): 3509 cm-1 (OH (strain band), 3169 cm-1 (NH strain band), 3028 cm-1 (ar CH strain band) (band), 2970, 2928, 2855 cm-1 (aldehyde CH asymmetric and symmetric stretching band), 1682 cm-1 (amide C=O stretching band), 1578 cm-1 (hydrazone C=N stretching band), 1509 cm-1 (aromatic C=C tensile, amide II NH bending and CN tensile 20 combination bands), 1449, 1359 cm-1 (aldehyde CH asymmetric and symmetric stretch band), 1225 cm-1 (CS stretch band), 1158 cm-1 (aromatic CF (stretch band), 842 cm-1 (1,4-disubstituted aromatic CH stretch band) peaks It includes.

24. According to claim 21, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-25 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,3-dihydroxyphenyl)methylidene]acetohydrazide The 1H-NMR spectrum of the molecule (Formula 2b), 1H-NMR (500 MHz) (DMSO- d6) δ (ppm): 11.98 and 11.62 (2s, 1H, CONH); 10.75 (br.s., 1H, OH); 9.56 (br.s., 1H,OH); 8.38 and 8.31 (2s, 1H, N=CH); 7.78 (d, J: 1.8 Hz, 1H, furan C5-H); 7.64- 7.60 (m, 2H, FPhC2,6-H); 7.47 (td, J: 8.73; 2.09 Hz; 2H, FPhC3.5-H); 7.1 (d, J: 30 7.8, 1H aromatic C6-H); 6.85 (d, J: 7.8, 1H, aromatic C4-H); 6.68 (t, J: 7.8 Hz, 1H, aromatic C5-H); 6.54 (dd J: 3.3; 1.8 Hz, 1H, furan C4-H); 6.24 (d, J: 3.3 Hz, 1H, furan C3-H); includes peaks of 4.47 and 4.09 (2s, 2H, SCH2). 56 25. A molecule according to claim 21, whose characteristic is; its 13C-NMR spectrum, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.46 and 163.60 (C=O); 163.2 (d, J: 248 Hz); 151.99; 148.57 and 142.78 (C=N); 147.83; 146.44; 146.03; 145.38; 141.37; 130.69 (d, J: 9.04 Hz); 130.11 (d, J: 2.76 Hz); 120.27; 119.67; 119.17; 117.92; Peaks 117.18; 117.49 (d, J: 23.29 Hz); 112.16; 111.80; 35.74 and 35.

35. It includes.

26. According to claim 21, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,3-dihydroxyphenyl)methylidene]acetohydrazide The electrospray ionization mass spectrum of the molecule (Formula 2b) is shown in ESI. HRMS: [M+H]+: includes peaks m / z 454.0990 and [MH]+: m / z 452.0845. 10 27. According to claim 21, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,3-dihydroxyphenyl)methylidene]acetohydrazide The molecular mass of the molecule (Formula 2b) is 453.0907 g / mol.

28. According to claim 21, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2,3-dihydroxyphenyl)methylidene]acetohydrazide 15 The molecule (Formula 2b) contains 54.76% C, 3.547% H, and 15.21% N by mass.

29. According to claims 11 and 12, it is a molecule whose property is; R1 is "Formula c". If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- [il]sulfanil]-N'-[(2-hydroxy-4-diethylaminophenyl)methylidene]acetohydrazidine (Formula 2c) is to obtain it. 20 30. According to claim 29, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-4 [diethylaminophenyl)methylidene]acetohydrazide molecule (Formula 2c) melting point Its temperature should be in the range of 247-249°C.

31. According to claim 29, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-25 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-4 diethylaminophenyl)methylidene] The FTIR spectrum of the acetohydrazide molecule (Formula 2c), FTIR ν (cm-1): 3183 cm-1 (NH stretching band), 3051 cm-1 (ar CH stretching band), 2976, 2932, 2870 cm-1 (aldehyde CH asymmetric and symmetric stretching band), 1664 cm-1 (amide C=O stretching band), 1600 cm-1 (hydrazone C=N stretching band), 1509 cm-1 30 (combination of aromatic C=C stretching, amide II NH bending and CN stretching) bands), 1356 cm-1 (aldehyde CH asymmetric and symmetric stretch band) 1224 cm- 1 (CS stretching band), 1197 cm-1 (aromatic CF stretching band), 848 cm-1 (1,4- It contains disubstituted aromatic CH (stretch band) peaks. 57 32. According to claim 29, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-4-diethylaminophenyl)methylidene] The 1H-NMR spectrum of the acetohydrazide molecule (Formula 2c), 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.66 and 11.33 (2s, 1H, CONH); 11.10 (s, 1H, OH); 8.18 and 8.11 (2s, 2H, N=CH); 7.77 (d, J = 1.8 Hz, 1H, furan C5-H); 7.63-7.60 (m, 5 2H, FPhC2,6-H); 7.47 (t, J: 8.7 Hz, 2H, FPhC3.5-H); 7.21 (d, J: 8.92 Hz, 1H, aromaticC6-H); 6.54 (dd, J = 3.54; 1.8 Hz, 1H, furan C4-H); 6.22-6.27 (m, 2H, furan C3-H and aromaticC5-H), 6.10 (d, J: 2.4 Hz, 1H, aromaticC3-H); 4.41 and 4.01 (2s, 2H, SCH2); 3.35 (N-CH2CH3, with DMSO peaks); 1.1 (t, J: 7.0 Hz, 6H, It contains peaks of 2N-CH2CH3). 10 33. According to claim 29, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-4-diethylaminophenyl)methylidene] Mass electrospray ionization of acetohydrazide molecule (Formula 2c) of the spectrum, ESI-HRMS: [M+H]+: m / z 509.1781 and [MH]+: m / z 507.1614 It includes its peaks. 15 34. According to claim 29, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-4-diethylaminophenyl)methylidene] acetohydrazide molecule (Formula 2c) has 58.70%C 5.095%H by mass and It contains 16.49% N.

35. According to claim 29, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-20 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-4-diethylaminophenyl)methylidene] The molecular weight of acetohydrazide molecule (Formula 2c) is 508.1692 g / mol It is the fact that.

36. A molecule according to claim 11 or 12, whose property is; R1 as "Formula d" If selected, the resulting molecule is 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-25 4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-3- [methoxyphenyl]methylidene]acetohydrazide (Formula 2d) is the formula.

37. According to claim 36, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-3-methoxyphenyl)methylidene]acetohydrazide The melting point of the molecule (Formula 2d) is 211-214°C. 30 38. According to claim 36, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-3-methoxyphenyl)methylidene]acetohydrazide The FTIR spectrum of the molecule (Formula 2d) has an FTIR ν (cm-1): 3534 cm-1 (OH (strain band), 3162 cm-1 (NH strain band), 3063 cm-1 (ar CH strain band) 58 (band), 2974, 2930, 2838 cm-1 (aldehyde CH asymmetric and symmetric stretching band), 1674 cm-1 (amide C=O stretching band), 1605 cm-1 (hydrazone C=N stretching band), 1511 cm-1 (aromatic C=C tensile, amide II NH bending and CN tensile) combination bands), 1456, 1382 cm-1 (aldehyde CH asymmetric and symmetric stretch band), 1226 cm-1 (CS stretch band), 1184 cm-1 (aromatic CF 5 (stretch band), 849 cm-1 (1,4-disubstituted aromatic CH stretch band) peaks It includes.

39. According to claim 36, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-3-methoxyphenyl)methylidene]acetohydrazide The 1H-NMR spectrum of the molecule (Formula 2d), 1H-NMR (500 MHz) (DMSO-10 d6) δ (ppm): 11.92 and 11.60 (2s, 1H, CONH); 10.57 (s, 1H, OH); 8.40 and 8.32 (2s, 2H, N=CH); 7.77 (d, J: 1.7 Hz, 1H, furan C5-H); 7.63-7.60 (m, 2H, FPhC2,6- H); 7.47 (td, 2H, J: 8.81, 2.15 Hz, FPhC3,5-H); 7.15 (dd, J: 8; 1.3 Hz, aromatik C6-H); 7.03 (dd, J: 8, 1.3 Hz, aromatik C4-H); 6.85 (t, J: 8 Hz, aromatik C5-H); 6.51 (dd, J: 3.6, 1.7 Hz, 1H, furan C4-H); 6.21 (d, J: 3.6 Hz, 1H, furan C3-H); 15 4.44 ve 4.05 (2s, 2H, SCH2); 3.79 (s, 3H, OCH3) piklerini içermesidir.

40. It has been 36 years since the beginning of the year; 2-[[4-(4-Florofenil)-5-(furan-2-il)-4H- 1,2,4-triazol-3-il]sulfanil]-N'-[(2-hidroksi-3-metoksifenil)metiliden]asetohidrazid molekülünün (Formül 2d) 13C-NMR spektrumunun, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.57 vs 163.56 (C=O); 163,21 (d, J: 248 Hz); 151,97; 20 151,65; 148,46; 147,82; 147.54 vs 141.66 (C=N); 145,32; 141,31; 130,71 (d, J: 9.13 Hz); 130.14 (d, J: 2.76 Hz); 120,87; 119,54; 119,36; 117,46 (d, J: 23 Hz); It includes peaks of 114.25; 112.15; 111.87; 56.31; 35.69 and 35.

3.

41. According to claim 36, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-3-methoxyphenyl)methylidene]acetohydrazide 25 The electrospray ionization mass spectrum of the molecule (Formula 2d) is shown in ESI. HRMS: This includes the peaks [M+H]+: m / z 468.1148 and [MH]+: m / z 466.0985.

42. According to claim 36, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-3-methoxyphenyl)methylidene]acetohydrazide The molecule (Formula 2d) contains 56.00% C, 4.508% H, and 14.24% N by mass. 30 43. According to claim 36, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(2-hydroxy-3-methoxyphenyl)methylidene]acetohydrazide The molecular mass of the molecule (Formula 2d) is 467.1063 g / mol. 59 44. A molecule according to claim 11 or 12, whose property is; R1 as "Formula e". If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- Obtaining the molecule [il]sulfanil]-N'-[(4-ethylphenyl)methylidene]acetohydrazide (Formula 2e) It is done.

45. According to claim 44, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-5 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-ethylphenyl)methylidene]acetohydrazide molecule (Formula 2e) states that the melting point is 190-192.5°C.

46. ​​According to claim 44, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-ethylphenyl)methylidene]acetohydrazide molecule (Formula 2e) FTIR spectrum, FTIR ν (cm-1): 3172, 3113 cm-1 (NH strain 10 band), 3077 cm-1 (ar CH stretching band), 2962, 2932, 2872 cm-1 (aldehyde CH asymmetric and symmetrical stretching band), 1672 cm-1 (amide C=O stretching band), 1617 cm-1 (hydrazone C=N stretching band), 1508 cm-1 (aromatic C=C stretching, amide II NH bending and CN stretching combination bands), 1473, 1430, 1383 cm-1 (aldehyde CH asymmetric and symmetric stretch band), 1222 cm-1 (CS strain 15 band), 1154 cm-1 (aromatic CF stretching band), 832 cm-1 (1,4-disubstituted It contains aromatic CH (stretch band) peaks.

47. According to claim 44, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-ethylphenyl)methylidene]acetohydrazide molecule (Formula 2e) 1H-NMR spectrum, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 20 11.62 (s, 1H, CONH); 8.15 and 7.98 (2s, 1H, N=CH); 7.78 (d, J: 1.7 Hz, 1H, furan C5-H); 7.63-7.59 (m, 2H, FPhC2,6-H); 7.57 (d, J: 8.11 Hz, 2H, aromatic C2,6-H); 7.47 (td, 2H, J: 8.76, 2.4 Hz, FPhC3.5-H); 7.28 (d, J: 8.11 Hz, 2H, aromatic C3,5- H); 6.54 (dd, J: 3.6, 1.7 Hz, 1H, furan C4-H); 6.22 (d, J: 3.6 Hz, 1H, furan C3-H); 4.46 and 4.06 (2s, 2H, SCH2); 2.65 (Ar-CH2-CH3, with DMSO peaks); 1.19 25 is the absorption of (t, J: 7.58 Hz, 3X, Ar-CH2-CH3) peaks.

48. Istem 44'e gore single molecule nucleus; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- of 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-ethylphenyl)methyldene]acetohydrazide molecule (Formula 2e) 13C-NMR spectrum, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.77 and 163.56 (C=O); 163.2 (d, J: 248 Hz); 151.95; 147.84; 147.63 30 and 144.44 (C=N); 146.51; 145.34; 141.39; 131.92; 130.71 (d, J: 9.41 Hz); 130.15 (d, J: 3.14 Hz); 128.71; 127.40; 117.46 (d, J: 23.15 Hz); 112.13; 111.76; 35.67 and includes the peaks of 35.62; 28.55; 15.

82. 60 49. According to claim 44, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-ethylphenyl)methylidene]acetohydrazide molecule (Formula 2e) electrospray ionization mass spectrum, ESI-HRMS: [M+H]+: It includes peaks m / z 450.1406 and [MH]+: m / z 448.1259.

50. According to claim 44, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-5 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-ethylphenyl)methylidene]acetohydrazide molecule (Formula 2e) contains 60.71% C, 4.877% H, and 15.09% N by mass.

51. According to claim 44, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-ethylphenyl)methylidene]acetohydrazide molecule (Formula 2e) has a molecular weight of 449.1321 g / mol. 10 52. According to claims 11 and 12, it is a molecule whose property is; R1 is represented by the "Formula f". If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- [il]sulfanil]-N'-[(2,4-dinitrophenyl)methylidene]acetohydrazidine (Formula 2f) is obtained. It is done.

53. According to claim 52, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-15 1,2,4-triazol-3-yl]sulfanil]-N'-[(2,4-dinitrophenyl)methylidene]acetohydrazide (Formula 2f) The melting point of the molecule is 121-123.5°C.

54. According to claim 52, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(2,4-dinitrophenyl)methylidene]acetohydrazide (Formula 2f) The FTIR cm-1 spectrum of the molecule, FTIR ν (cm-1): 3470 cm-1 (NH stretching 20 band), 3089 cm-1 (ar CH stretching band), 2933, 2833 cm-1 (aldehyde CH asymmetric and symmetric stretching band), 1681 cm-1 (amide C=O stretching band), 1599 cm-1 (hydrazone C=N stretching band), 1544 cm-1 (NITRO structure NO asymmetric) (stretch band), 1509 cm-1 (aromatic C=C stretching, amide II NH bending and CN (stress combination bands), 1438 (aldehyde CH asymmetric and symmetric stretching 25 band), 1339 cm-1 (NO symmetric stretching band belonging to nitro structure), 1225 cm-1 (C- S stretching band), 1153 cm-1 (aromatic CF stretching band), 838 cm-1 (1,4- It contains disubstituted aromatic CH (stretch band) peaks.

55. According to claim 52, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(2,4-dinitrophenyl)methylidene]acetohydrazide (Formula 2f) 30 1H-NMR spectrum of the molecule, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 12.36 and 12.18 (2s, 1H, CONH); 8.78 (s, 1H, aromaticC3-H); 8.55 (d, 1H, J: 8.65 Hz, aromatic C5-H); 8.32 (d, 1H, J: 8.65 Hz, aromatic C6-H); 8.67 and 8.47 (2h, 1H, N=CH); 7.77 (s, 1H, furan C5-H); 7.63-7.60 (m, 2H, FPhC2,6-H); 7.48 (t, J: 8.72 61 Hz, 2H, FPhC3,5-H); 6.53 (s, 1H, furan C4-H); 6.20 (s, 1H, furan C3-H); 4.48 and It contains peaks of 4.12 (2s, 2H, SCH2).

56. According to claim 52, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(2,4-dinitrophenyl)methylidene]acetohydrazide (Formula 2f) The 13C-NMR spectrum of the molecule, 13C-NMR (APT) (125 MHz) (DMSO-d6) 5 δ (ppm): 169.54 and 164.54 (C=O), 163.22 (d, J: 248.28 Hz), 151.60, 148.02, 147.87, 147.65, 145.35, 141.60 and 138.38 (C=N), 141.32, 134.32, 130.68 (d, J: 9.19 Hz), 130.09 (d, J: 2.98 Hz), 129.98, 127.99, 120.78, 117.49 (d, J: 23.51 (Hz), including peaks of 112.11, 111.80, 35.59 and 35.

30.

57. According to claim 52, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-10 1,2,4-triazol-3-yl]sulfanil]-N'-[(2,4-dinitrophenyl)methylidene]acetohydrazide (Formula 2f) The electrospray ionization mass spectrum of the molecule, ESI-HRMS: [M+H]+ contains the peaks m / z 512.0797 and [MH]+ contains the peaks m / z 510.0648.

58. According to claim 52, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(2,4-dinitrophenyl)methylidene]acetohydrazide (Formula 2f) 15 The molecule contains 49.45% C, 3.224% H, and 18.27% N by mass.

59. According to claim 52, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(2,4-dinitrophenyl)methylidene]acetohydrazide (Formula 2f) The molecular mass of the molecule is 511.0710 g / mol.

60. A molecule according to claim 11 or 12, whose property is; R1 as "Formula g" 20 If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- [il]sulfanil]-N'-[(3,4,5-trimethoxyphenyl)methylidene]acetohydrazidine (Formula 2g) is obtained. It is done.

61. According to claim 60, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4,5-trimethoxyphenyl)methylidene]acetohydrazide 25 The melting point of the molecule (Formula 2g) is 176-179°C.

62. According to claim 60, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4,5-trimethoxyphenyl)methylidene]acetohydrazide The FTIR spectrum of the molecule (Formula 2g) has an FTIR ν (cm-1): 3148 cm-1 (NH3). (stretch band), 3072 cm-1 (ar CH stretch band), 2978, 2935, 2872 cm-1 30 (aldehyde CH asymmetric and symmetric stretching band), 1650 cm-1 (amide C=O stretching band), 1600 cm-1 (hydrazone C=N stretching band), 1509 cm-1 (aromatic C=C strain, amide II NH bending and CN strain combination bands), 1436, 1372 cm-1 (aldehyde CH asymmetric and symmetric stretch band), 1223 cm-1 (CS stretch 62 band), 1125 cm-1 (aromatic CF stretching band), 846 cm-1 (1,4-disubstituted It contains aromatic CH (stretch band) peaks.

63. According to claim 60, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4,5-trimethoxyphenyl)methylidene]acetohydrazide The 1H-NMR spectrum of the molecule (Formula 2g), 1H-NMR (500 MHz) (DMSO-5 d6) δ (ppm): 11.74 and 11.69 (2s, 1H, CONH); 8.12 and 7.92 (2s, 1H, N=CH); 7.78 (d, J: 1.8 Hz, 1H, furan C5-H); 7.64-7.60 (m, 2H, FPhC2,6-H); 7.50-7.45 (m, 2H, FPhC3,5-H); 7.01 and 6.99 (2s, 2H, aromatic C2,6-H); 6.54 (dd, J: 3.5, 1.8 Hz, 1H, furan C4-H); 6.24 (d, J: 3.5 Hz, 1H, furan C3-H); 4.46 and 4.08 (2s, 2H, SCH2); Peaks 3.81 and 3.83 (2s, 6H, Ph3,5-OCH3); 3.69 and 3.71 (2s, 3H, Ph4-OCH3) were observed in 10 It includes.

64. According to claim 60, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4,5-trimethoxyphenyl)methylidene]acetohydrazide The 13C-NMR spectrum of the molecule (Formula 2g), 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.93 and 163.66 (C=O), 163.20 (d, J: 248.11 Hz), 153.61, 15 151.72, 147.85, 147.63 and 144.13 (C=N), 145.31, 141.36, 139.59, 130.68 (d, J: 9.18 Hz), 130.13 (d, J: 3.05 Hz), 129.92, 117.43 (d, J: 23.5 Hz), 112.12, 111.77, It includes peaks of 104.65, 60.57, 56.36, 35.63 and 35.

16.

65. According to claim 60, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4,5-trimethoxyphenyl)methylidene]acetohydrazide 20 The electrospray ionization mass spectrum of the molecule (Formula 2g) was determined using ESI. HRMS: This includes the peaks [M+H]+: m / z 512.1415 and [MH]+: m / z 510.1263.

66. According to claim 60, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4,5-trimethoxyphenyl)methylidene]acetohydrazide The molecule (Formula 2g) contains 55.21% C, 4.683% H, and 13.25% N by mass.

67. According to claim 60, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4,5-trimethoxyphenyl)methylidene]acetohydrazide The molecular mass of the molecule (Formula 2g) is 511.1325 g / mol.

68. A molecule according to claim 11 or 12, whose property is; R1 as "Formula h". If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-30 [il]sulfanil]-N'-[(4-nitrophenyl)methylidene]acetohydrazidine (Formula 2h) is obtained. It is done. 63 69. According to claim 68, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-nitrophenyl)methylidene]acetohydrazide molecule (Formula 2h) has a melting point of 107-109°C.

70. According to claim 68, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 5 of the 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-nitrophenyl)methylidene]acetohydrazide molecule (Formula 2h) FTIR spectrum, FTIR ν (cm-1): 3155 cm-1 (NH stretching band), 3026 cm-1 (ar CH stretching band), 2971, 2877 cm-1 (aldehyde CH asymmetric and symmetrical stretching band), 1687 cm-1 (amide C=O stretching band), 1589 cm-1 (hydrazone C=N stretching band), 1567 cm-1 (NITRO structure NO asymmetric) (stretch band), 1509 cm-1 (aromatic C=C stretching, amide II NH bending and CN 10 (strain combination bands), 1453, 1340 cm-1 (aldehyde CH asymmetric and symmetrical stretch band), 1340 cm-1 (NO symmetrical stretch of nitro structure) CF stretch band), 1233 cm-1 (CS stretch band), 1185 cm-1 (aromatic CF stretch band), It contains peaks of 839 cm-1 (1,4-disubstituted aromatic CH stretching band).

71. According to claim 68, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-15 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-nitrophenyl)methylidene]acetohydrazide molecule (Formula 2h) 1H-NMR spectrum, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.97 (s, 1H, CONH); 8.27 (d, J: 8.9 Hz, 2H, aromatic C3,5-H); 8.11 (s, 1H, N=CH); 7.93 (d, J: 8.9, 2H, aromatic C2,6-H); 7.76 (d, J: 1.8 Hz, 1H, furan C5-H); 7.64-7.60 (m, 2H, FPhC2,6-H); 7.47 (t, J: 8.7 Hz, 2H, FPhC3,5-H); 6.53 (dd, J: 20 3.5, 1.8 Hz, 1H, furan C4-H); 6.22 (d, J: 3.5 Hz, 1H, furan C3-H); 4.5 and 4.11 (2s, It contains 2H, SCH2) peaks.

72. According to claim 68, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-nitrophenyl)methylidene]acetohydrazide molecule (Formula 2h) 13C-NMR spectrum, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ 25 (ppm): 169.32 and 164.26 (C=O), 163.21 (d, J: 248.18 Hz), 151.76, 148.18, 147.88, 145.32, 145.19 and 142.05 (C=N), 141.31, 140.62, 130.66 (d, J: 9.15 Hz), 130.09 (d, J: 2.76 Hz), 128.23, 124.45, 117.48 (d, J: 23.56 Hz), 112.11, It includes peaks of 111.82, 35.62 and 35.

45.

73. According to claim 68, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-30 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-nitrophenyl)methylidene]acetohydrazide molecule (Formula 2h) electrospray ionization mass spectrum, ESI-HRMS: [M+H]+: It includes peaks m / z 467.0943 and [MH]+: m / z 465.0796. 64 74. According to claim 68, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-nitrophenyl)methylidene]acetohydrazide molecule (Formula 2h) It contains 49.94% C, 3.829% H and 16.19% N.

75. According to claim 68, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 5 of the 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-nitrophenyl)methylidene]acetohydrazide molecule (Formula 2h) has a molecular weight of 466.0859 g / mol.

76. A molecule according to claim 11 or 12, whose property is; R1 as "Formula i". If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- [il]sulfanil]-N'-[(4-methylphenyl)methylidene]acetohydrazidine (Formula 2i) is obtained. It is done. 10 77. According to claim 76, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-methylphenyl)methylidene]acetohydrazide molecule (Formula 2i) states that the melting point is 167-169.5°C.

78. According to claim 76, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-methylphenyl)methylidene]acetohydrazide molecule 15 (Formula 2i) FTIR spectrum, FTIR ν (cm-1): 3167 cm-1 (NH stretching band), 3080 cm-1 (ar CH stretching band), 2959, 2924 cm-1 (aldehyde CH asymmetric and symmetrical stretching band), 1671 cm-1 (amide C=O stretching band), 1617 cm-1 (hydrazone C=N stretching band), 1508 cm-1 (aromatic C=C stretching, amide II NH bending and CN tensile combination bands), 1429, 1382 cm-1 (aldehyde CH 20 asymmetric and symmetric stretch band), 1222 cm-1 (CS stretch band), 1155 cm- 1 (aromatic CF stretching band), 843 cm-1 (1,4-disubstituted aromatic CH stretching band) (band) includes peaks.

79. According to claim 76, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 25 of the molecule 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-methylphenyl)methylidene]acetohydrazide (Formula 2i) 1H-NMR spectrum, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.69 and 11.61 (s, 1H, CONH); 8.15 and 7.97 (s, 1H, N=CH); 7.77 (d, J: 1.8 Hz, 1H, furan C5-H); 7.63-7.59 (m, 2H, FPhC2,6-H); 7.55 (d, J: 8.07 Hz, 2H, aromatic C 2,6 -H); 7.47 (td, J: 8.7; 1.72 Hz, 2H, FPhC3,5-H); 7.24 (d, J: 8.07 Hz, 2H, aromatic C 3,5 -H); 6.53 (dd, J: 3.57, 1.71 Hz, 1H, furan C4-H); 6.22 (d, J: 30 3.57 Hz, 1H, furan C3-H); 4.46 and 4.06 (2s, 2H, SCH2), 2.33 (s, 3H, PhCH3) It includes its peaks.

80. According to claim 76, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-methylphenyl)methylidene]acetohydrazide molecule 65 (Formula 2i) 13C-NMR spectrum, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.77 and 163.58 (C=O), 163.20 (d, J: 248.23 Hz), 151.96, 147.84, 147.67 and 144.48 (C=N), 145.32, 141.40, 140.28, 131.67, 130.70 (d, J: 9.19 Hz), 130.15 (d, J: 2.75 Hz), 129.89, 127.31, 117.45 (d, J: 23.46 Hz), 112.12, It includes peaks of 111.77, 35.69 and 35.63, 21.

49. 5 81. According to claim 76, it is a molecule and its property is; According to claim 76, it is a molecule. Its feature is; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanil]-N'-[(4- Electrospray of [methylphenyl]methylidene]acetohydrazide molecule (Formula 2i) Ionization mass spectrum, ESI-HRMS: [M+H]+: m / z 436.1249 and [MH]+: m / z includes peaks 434.1102. 10 82. According to claim 75, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-methylphenyl)methylidene]acetohydrazide molecule (Formula 2i) contains 57.98% C, 4.228% H, and 15.09% N by mass.

83. According to claim 76, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-methylphenyl)methylidene]acetohydrazide molecule 15 (Formula 2i) has a molecular weight of 435.1165 g / mol.

84. A molecule according to claim 11 or 12, whose property is; R1 as "Formula j". If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- [il]sulfanil]-N'-[(3,4-dimethoxyphenyl)methylidene]acetohydrazidine (Formula 2j) is obtained. It is done. 20 85. According to claim 84, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4-dimethoxyphenyl)methylidene]acetohydrazide The melting point of the molecule (Formula 2j) is 200-202.5°C.

86. According to claim 84, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4-dimethoxyphenyl)methylidene]acetohydrazide 25 The FTIR spectrum of the molecule (Formula 2j) has an FTIR ν (cm-1): 3168, 3108 cm-1 (NH stretching band), 3082 cm-1, 3029, 3003 cm-1 (CH stretching band), 2981, 2925, 2837 cm-1 (aldehyde CH asymmetric and symmetric stretching band), 1678 cm-1 (amide C=O stretching band), 1598 cm-1 (hydrazone C=N stretching band), 1509 cm- 1 (aromatic C=C stretching, amide II NH bending and CN stretching combination 30 bands), 1462, 1435, 1385 cm-1 (aldehyde CH asymmetric and symmetric stretching CF stretch band), 1221 cm-1 (CS stretch band), 1143 cm-1 (aromatic CF stretch band), It contains peaks of 844 cm-1 (1,4-disubstituted aromatic CH stretching band). 66 87. According to claim 84, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4-dimethoxyphenyl)methylidene]acetohydrazide The 1H-NMR spectrum of the molecule (Formula 2j), 1H-NMR (500 MHz) (DMSO- d6) δ (ppm): 11.62 and 11.56 (2s, 1H, CONH); 8.11 and 7.92 (s, 1H, N=CH); 7.77 (d, J: 1.8 Hz, 1H, furan C5-H); 7.63-7.59 (m, 2H, FPhC2,6-H); 7.49-7.45 (m, 2H, 5 FPhC3,5-H); 7.30 (d, 1H, J: 1.94 Hz, aromatic C2-H); 7.22 (dd, 1H, J: 8.31; 1.94 Hz, aromatic C6-H); 7.02 (d, 1H, J: 8.31 Hz, aromatic C5-H); 6.53 (dd, J: 3.5, 1.8 Hz, 1H, furan C4-H); 6.22 (d, J: 3.5 Hz, 1H, furan C3-H); 4.45 and 4.05 (2s, 2H, This includes peaks of 3.8 (s, 3H, Ph-3OCH3) and 3.79 (s, 3H, Ph-4OCH3) in SCH2.

88. According to claim 84, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-10 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4-dimethoxyphenyl)methylidene]acetohydrazide The 13C-NMR spectrum of the molecule (Formula 2j) is shown in 13C-NMR (APT) (125 MHz) format. (DMSO-d6) δ (ppm): 168.70 and 163.40 (C=O), 163.20 (d, J: 248.12 Hz), 151.72, 151.05, 149.43, 147.84, 147.79 and 144.36 (C=N), 145.32, 141.39, 130.71 (d, J: 9.18 Hz), 130.15 (d, J: 3.24 Hz), 127.11, 121.56, 117.45 (d, J: 22.99 Hz), 15 The peaks were 112.13, 111.98, 111.84, 109.21, 56.01, 55.89, 35.67 and 35.

35. It includes.

89. According to claim 84, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4-dimethoxyphenyl)methylidene]acetohydrazide The electrospray ionization mass spectrum of the molecule (Formula 2j) is shown in ESI-20 HRMS: This includes the peaks [M+H]+: m / z 482.1304 and [MH]+: m / z 480.1159.

90. According to claim 84, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4-dimethoxyphenyl)methylidene]acetohydrazide The molecule (Formula 2j) contains 57.21% C, 4.370% H, and 14.53% N by mass.

91. According to claim 84, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-25 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3,4-dimethoxyphenyl)methylidene]acetohydrazide The molecular mass of the molecule (Formula 2j) is 481.1220 g / mol.

92. A molecule according to claim 11 or 12, whose property is; R1 as "Formula k". If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- This is the preparation of [il]sulfanil]-N'-[(4-methoxy)methylidene]acetohydrazidine (Formula 2k). 30 93. According to claim 92, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-methoxy)methylidene]acetohydrazide molecule (Formula 2k) has a melting point of 194-195.5 °C. 67 94. According to claim 92, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-methoxy)methylidene]acetohydrazide molecule (Formula 2k) FTIR spectrum, FTIR ν (cm-1): 3105 cm-1 (NH stretching band), 3078 cm-1 (ar CH stretching band), 2966 cm-1 (aldehyde CH asymmetric and symmetric) 1681 cm-1 (stress band), 1666 cm-1 (amide C=O stretching band), 1666 cm-1 (hydrazone C=N 5 (stretch band), 1602 cm-1 (aromatic C=C stretching, amide II NH bending and CN strain combination bands), 1453, 1377 cm-1 (aldehyde CH asymmetric and symmetrical stretch band), 1221 cm-1 (CS stretch band), 1173 cm-1 (aromatic CF stretching band), 831 cm-1 (1,4-disubstituted aromatic CH stretching band) It includes its peaks. 10 95. According to claim 92, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-methoxy)methylidene]acetohydrazide molecule (Formula 2k) 1H-NMR spectrum, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.54 and 11.47 (s, 1H, CONH); 8.05 and 7.87 (s, 1H, N=CH); 7.70 (d, J: 1.7 Hz, 1H, furan C5-H); 7.58-7.64 (m, 2H, FPhC2,6-H); 7.53 (d, J: 8.76 Hz, 2H, aromatic 15 C2,6-H); 7.39 (t, J: 8.7 Hz, 2H, FPhC3,5-H); 6.92 (d, J: 8.76 Hz, 2H, aromatic C3,5- H); 6.46 (dd, J: 3.5, 1.7 Hz, 1H, furan C4-H); 6.14 (d, J: 3.5 Hz, 1H, furan C3-H); It includes peaks of 4.37 and 3.97 (2s, 2H, SCH2).

96. According to claim 92, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 20 molecules of 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-methoxy)methylidene]acetohydrazide (Formula 2k) 13C-NMR spectrum, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.64 and 163.44 (C=O), 163.21 (d, J: 248.32 Hz), 161.21, 151.74, 147.84, 147.53 and 144.28 (C=N), 145.31, 141.40, 130.69 (d, J: 9.18 Hz), 130.15 (d, J: 2.74 Hz), 128.92, 126.95, 117.45 (d, J: 23.39 Hz), 114.76, 112.12, 111.77, It includes peaks of 55.73, 35.70 and 35.

66. 25 97. According to claim 92, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-methoxy)methylidene]acetohydrazide molecule (Formula 2k) electrospray ionization mass spectrum, ESI-HRMS: [M+H]+: It includes the peaks m / z 452.1174 and [MH]+: m / z 450.1040.

98. According to claim 92, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-30 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-methoxy)methylidene]acetohydrazide molecule (Formula 2k) contains 58.41% C, 3.953% H, and 15.32% N by mass. 68 99. According to claim 92, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-methoxy)methylidene]acetohydrazide molecule (Formula 2k) has a molecular weight of 451.1114 g / mol.

100. A molecule according to claim 11 or 12, whose property is; R1's "Formula 1" If selected as 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-5 [il]sulfanil]-N'-[(4-cyanophenyl)methylidene]acetohydrazidine (Formula 2l) is obtained. It is done.

101. According to claim 100, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2- yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-cyanophenyl)methylidene]acetohydrazide The melting point of the molecule (Formula 2l) is 232-234.5°C. 10 102. According to claim 100, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2- yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-cyanophenyl)methylidene]acetohydrazide The FTIR spectrum of the molecule (Formula 2l) has an FTIR ν (cm-1): 3190 cm-1 (NH3). (stretch band), 3101, 3011 cm-1 (ar CH stretch band), 2929, 2864 cm-1 (aldehyde CH asymmetric and symmetric stretching band), 2221 cm-1 (C≡N stretching 15 (stretch band), 1681 cm-1 (amide C=O gb), 1575 cm-1 (hydrazone C=N stretching band), 1508 cm-1 (aromatic C=C tensile, amide II NH bending and CN tensile) combination bands), 1454, 1361 cm-1 (aldehyde CH asymmetric and symmetric stretch band), 1227 cm-1 (CS stretch band), 1153 cm-1 (aromatic CF (stretch band), 839 cm-1 (1,4-disubstituted aromatic CH stretch band) peaks 20 It includes.

103. According to claim 100, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2- yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-cyanophenyl)methylidene]acetohydrazide The 1H-NMR spectrum of the molecule (Formula 2l), 1H-NMR (500 MHz) (DMSO- d6) δ (ppm): 12.02 and 11.92 (2s, 1H, CONH); 8.26 and 8.05 (2s, 1H, N=CH); 7.88 25 (d, J=8.1 Hz, 2H, CN-PhC2,6-H); 7.85 (d, J: 8.1 Hz, 2H, CN-PhC3,5-H); 7.77 (d, J: 1.8 Hz, 1H, furan C5-H); 7.64-7.60 (m, 2H, FPhC2,6-H); 7.47 (t, J: 8.7 Hz, 2H, FPhC3,5-H); 6.53 (dd, J: 3.5, 1.8 Hz, 1H, furan C4-H); 6.24 (d, J: 3.5 Hz, 1H, furan C3-H includes peaks of 4.50 and 4.12 (2s, 2H, SCH2).

104. According to claim 100, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-30 yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-cyanophenyl)methylidene]acetohydrazide The 13C-NMR spectrum of the molecule (Formula 2l) is shown in 13C-NMR (APT) (125 MHz) format. (DMSO-d6) δ (ppm): 169.27 (C=O), 163.18 (d, J: 242.35 Hz), 151.78, 147.87, 145.64 and 142.42 (C=N), 145.33, 141.36, 138.81, 133.16, 130.68 (d, J: 9.23 69 Hz), 130.12 (d, J: 2.71 Hz), 127.89, 119.11, 117.47 (d, J: 23.02 Hz), 112.26, It includes peaks of 112.12, 111.79, 35.63 and 35.

51.

105. According to claim 100, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2- yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-cyanophenyl)methylidene]acetohydrazide The electrospray ionization mass spectrum of the molecule (Formula 2l) is shown in ESI-5 HRMS: This includes the peaks [M+H]+: m / z 447.1043 and [MH]+: m / z 445.0898.

106. According to claim 100, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2- yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-cyanophenyl)methylidene]acetohydrazide The molecule (Formula 2l) contains 58.49% C, 3.506% H, and 18.47% N by mass.

107. According to claim 100, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-10 yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-cyanophenyl)methylidene]acetohydrazide The molecular mass of the molecule (Formula 2l) is 446.0961 g / mol.

108. A molecule according to claim 11 or 12, whose property is; R1's "Formula m" If selected as 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- [il]sulfanil]-N'-[(4-hydroxyphenyl)methylidene]acetohydrazidine (Formula 2m) is obtained 15 It is done.

109. According to claim 108, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2- yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-hydroxyphenyl)methylidene]acetohydrazide The melting point of the molecule (Formula 2m) is 264.5-267°C.

110. According to claim 108, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-20 yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-hydroxyphenyl)methylidene]acetohydrazide The FTIR spectrum of the molecule (Formula 2m) has an FTIR ν (cm-1): 3202 cm-1 (NH3). (stretch band), 3064 cm-1 (ar CH stretch band), 2883, 2804 cm-1 (aldehyde C- H asymmetric and symmetric stretch band), 1659 cm-1 (amide C=O stretch band), 1603 cm-1 (hydrazone C=N stretching band), 1509 cm-1 (aromatic C=C stretching, 25 amide II NH bending and CN stretching combination bands), 1451, 1377 cm-1 (aldehyde CH asymmetric and symmetric stretch band), 1224 cm-1 (CS stretch band), 1144 cm-1 (aromatic CF stretching band), 849 cm-1 (1,4-disubstituted It contains aromatic CH (stretch band) peaks.

111. According to claim 108, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-30 yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-hydroxyphenyl)methylidene]acetohydrazide The 1H-NMR spectrum of the molecule (Formula 2m), 1H-NMR (500 MHz) (DMSO- d6) δ (ppm): 11.55 and 11.48 (2s, 1H, CONH); 9.93 (s, 1H, OH); 8.08 and 7.91 (2s, 1H, N=CH); 7.77 (d, J: 1.7 Hz, 1H, furan C5-H); 7.64-7.60 (m, 2H, FPhC2,6-H); 70 7.53 (d, J: 8.62 Hz, 2H, OH-PhC2,6-H); 7.48-7.45 (m, 2H, FPhC3,5-H); 6.82 (d, 2H, J: 8.62 Hz, OH-PhC3,5-H); 6.53 (dd, J: 3.5; 1.8 Hz, 1H, furan C4-H); 6.24 (d, J: 3.5 Hz, 1H, furan C3-H); includes peaks of 4.45 and 4.05 (2s, 2H, SCH2).

112. According to claim 108, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2- yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-hydroxyphenyl)methylidene]acetohydrazide 5 The 13C-NMR spectrum of the molecule (Formula 2m) is shown in 13C-NMR (APT) (125 MHz) format. (DMSO-d6) δ (ppm): 168.49 and 163.28 (C=O), 163.2 (d, J: 248.57 Hz), 159.80, 151.73, 147.82, 147.94 and 144.71 (C=N), 145.32, 141.38, 130.71 (d, J: 9.18 Hz), 130.14 (d, J: 3.15 Hz), 129.07, 125.38, 117.45 (d, J: 23.09 Hz), 116.17, It includes peaks of 112.13, 111.78, and 35.

70. 10 113. According to claim 108, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2- yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-hydroxyphenyl)methylidene]acetohydrazide The electrospray ionization mass spectrum of the molecule (Formula 2m) was determined using ESI. HRMS: This includes the peaks [M+H]+: m / z 438.1038 and [MH]+: m / z 436.0895.

114. According to claim 108, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-15 yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-hydroxyphenyl)methylidene]acetohydrazide The molecule (Formula 2m) contains 56.53% C, 3.748% H, and 15.62% N by mass.

115. According to claim 108, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2- yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-hydroxyphenyl)methylidene]acetohydrazide The molecular mass of the molecule (Formula 2m) is 437.0957 g / mol. 20 116. A molecule according to claim 11 or 12, whose property is; Formula n of R1. If selected as 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- [il]sulfanil]-N'-[(3-hydroxyphenyl)methylidene]acetohydrazidine (Formula 2n) is obtained. It is done.

117. According to claim 116, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-25 1,2,4-triazol-3-yl]sulfanil]-N'-[(3-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2n) has a melting point of 232-234.5°C.

118. According to claim 116, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(3-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2n) FTIR spectrum, FTIR ν (cm-1): 3157 cm-1 (NH stretching band), 30 3073 cm-1 (ar CH stretching band), 2962, 2830 cm-1 (aldehyde CH asymmetric and symmetrical stretching band), 1666 cm-1 (amide C=O stretching band), 1612 cm-1 (hydrazone C=N stretching band), 1510 cm-1 (aromatic C=C stretching, amide II NH bending and CN strain combination bands), 1440, 1383 cm-1 (aldehyde CH 71 (asymmetric and symmetric stretch band) 1225 cm-1 (CS stretch band), 1155 cm-1 (aromatic CF stretching band), 841 cm-1 (1,4-disubstituted aromatic CH stretching band) (band) includes peaks.

119. According to claim 116, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 5 of the 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2n) 1H-NMR spectrum, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.64 (s, 1H, CONH); 9.65 (2s, 1H, OH); 8.09 and 7.93 (2s, 1H, N=CH); 7.77 (d, J: 1.65 Hz, 1H, furan C5-H); 7.63-7.61 (m, 2H, FPhC2,6-H); 7.47 (t, J: 8.7 Hz, 2H, FPhC3,5-H); 7.24 (t, J: 7.81 Hz, aromatic C6-H); 7.16 (s, 1H, aromatic C2-H); 7.08 (d, J: 7.81 Hz, 1H, aromatic C5-H); 6.82 (d, J: 7.81 Hz, 1H, aromatic C4-H); 6.53 10 (dd, J: 3.53; 1.65 Hz, 1H, furan C4-H); 6.24 (d, J: 3.53 Hz, 1H, furan C3-H); 4.49 and contains 4.06 (2s, 2H, SCH2) peaks.

120. A molecule according to claim 116, characterized in that; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(3-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2n) 13C-NMR spectrum, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ 15 (ppm): 168.79 and 163.69 (C=O), 163.22 (d, J: 248.72 Hz), 158.13, 151.73, 147.83, 147.73 and 144.69 (C=N), 145.30, 141.38, 135.60, 130.69 (d, J: 9.19 Hz), 130.35, 130.11 (d, J: 3.21 Hz), 119.00, 117.88, 117.47 (d, J: 23.40 Hz), 113.02, It includes peaks of 112.12, 111.80, and 35.

71.

121. According to claim 116, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-20 1,2,4-triazol-3-yl]sulfanil]-N'-[(3-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2n) electrospray ionization mass spectrum, ESI-HRMS: [M+H]+: It includes the peaks m / z 438.1039 and [MH]+: m / z 436.0895.

122. According to claim 116, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 25 of the molecule 1,2,4-triazol-3-yl]sulfanil]-N'-[(3-hydroxyphenyl)methylidene]acetohydrazide (Formula 2n) contains 57.19% C, 3.62% H, and 15.81% N by mass.

123. According to claim 116, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(3-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2n) has a molecular weight of 437.0957 g / mol.

124. A molecule according to claim 11 or 12, whose property is; R1 as "Formula 0" 30 If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- This involves obtaining [il]sulfanil]-N'-[(4-chlorophenyl)methylidene]acetohydrazidine (Formula 20).

125. According to claim 124, it is a molecule and its characteristic is that its melting point is 117-119oC. It is the fact that. 72 126. According to claim 124, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-chlorphenyl)methylidene]acetohydrazide (Formula 2o) The FTIR spectrum of the molecule, FTIR ν (cm-1): 3178 cm-1 (NH stretching band), 3080 cm-1 (ar CH stretching band), 2954 cm-1 (aldehyde CH asymmetric and symmetric) (stretch band), 1672 cm-1 (amide C=O stretch band), 1615 cm-1 (hydrazone C=N 5 (stretch band), 1509 cm-1 (aromatic C=C stretching, amide II NH bending and CN strain combination bands), 1448, 1382 cm-1 (aldehyde CH asymmetric and symmetric stretch band), 1223 cm-1 (CS stretch band), 1125 cm-1 (aromatic CF stretch band) (band), 843 cm-1 (1,4-disubstituted aromatic CH stretching band) peaks It includes. 10 127. According to claim 124, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-chlorphenyl)methylidene]acetohydrazide (Formula 2o) 1H-NMR spectrum of the molecule, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.82 and 11.74 (2s, 1H, CONH); 8.20 and 8.01 (2s, 1H, N=CH); 7.77 (m, 1H, furan C5-H); 7.73 (d, J: 8.59 Hz, 2H, ClPhC2,6-H), 7.63-7.60 (m, 2H, FPhC2,6-H), 7.52-15 7.45 (m, 4H, FPhC3,5-H and ClPhC3,5-H); 6.53 (m, 1H, furan C4-H); 6.24 (d, J: 3.58 It includes peaks of 4.47 and 4.08 (2s, 2H, SCH2) (Hz, 1H, furan C3-H).

128. According to claim 124, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-chlorphenyl)methylidene]acetohydrazide (Formula 2o) The 13C-NMR spectrum of the molecule, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ 20 (ppm): 168.97 and 163.85 (C=O), 163.21 (d, J: 248.18 Hz), 151.89, 147.85, 146.34 and 143.13 (C=N), 145.32, 141.36, 134.92, 133.30, 130.68 (d, J: 9.22 Hz), 130.12 (d, J: 3.22 Hz), 129.35, 128.95, 117.46 (d, J: 23.30 Hz), 112.12, 111.80, 35.65 and It includes peaks of 35.

58.

129. According to claim 124, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-25 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-chlorphenyl)methylidene]acetohydrazide (Formula 2o) The electrospray ionization mass spectrum of the molecule, ESI-HRMS: [M+H]+: It includes peaks m / z 456.0703 and [MH]+: m / z 454.0557.

130. According to claim 124, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-chlorphenyl)methylidene]acetohydrazide (Formula 20) 30 It contains 52.9% C, 3.631% H, and 14.53% N by mass.

131. According to claim 124, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-chlorphenyl)methylidene]acetohydrazide (Formula 2o) Its molecular weight is 455.0619 g / mol. 73 132. A molecule according to claim 11 or 12, whose property is; R1 as "Formula p". If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- This involves obtaining [il]sulfanil]-N'-[(4-fluorphenyl)methylidene]acetohydrazidine (Formula 2p).

133. According to claim 132, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 5 of the 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-fluorphenyl)methylidene]acetohydrazide molecule (Formula 2p) states that the melting point is 129-131°C.

134. According to claim 132, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-fluorphenyl)methylidene]acetohydrazide molecule (Formula 2p) FTIR spectrum, FTIR ν (cm-1): 3180 cm-1 (NH stretching band), 3078 cm-1 (ar CH stretching band), 2964 cm-1 (aldehyde CH asymmetric and symmetric 10 (stretch band), 1671 cm-1 (amide C=O stretch band), 1600 cm-1 (hydrazone C=N (stretch band), 1509 cm-1 (aromatic C=C stretching, amide II NH bending and CN strain combination bands), 1427, 1383 cm-1 (aldehyde CH asymmetric and symmetrical stretch band), 1232 cm-1 (CS stretch band), 1155 cm-1 (aromatic C- F stretching band), 839 cm-1 (1,4-disubstituted aromatic CH stretching band) peaks 15 It includes.

135. According to claim 132, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-fluorphenyl)methylidene]acetohydrazide molecule (Formula 2p) 1H-NMR spectrum, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.7 (2s, 1H, CONH); 8.19 and 8.01 (2s, 1H, N=CH); 7.75-7.72 (m, 2H, N=C-20 FPhC2,6-H); 7.63-7.60 (m, 2H, FPhC2,6-H); 7.78 (m, 1H, furan C5-H); 7.47 (t, J: 8.74 Hz, 2H, FPhC3,5-H); 7.31-7.26 (m, 2H, N=C-FPhC3,5-H); 6.53 (dd, J: 3.57; 1.77 Hz, 1H, furan C4-H); 6.23 (d, J: 3.57 Hz, 1H, furan C3-H); 4.47 and 4.07 (2s, It contains 2H, SCH2) peaks.

136. According to claim 132, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-25 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-fluorphenyl)methylidene]acetohydrazide molecule (Formula 2p) 13C-NMR spectrum, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.90 and 163.75 (C=O), 163.50 (d, J: 247.76 Hz), 163.20 (d, J: 248.61 Hz), 151.70, 147.85, 146.52 and 143.25 (C=N), 145.32, 141.37, 130.99 (d, J: 2.78 Hz), 130.69 (d, J: 9.23 Hz), 130.13 (d, J: 3.23 Hz), 129.51 (d, J: 8.70 Hz), 117.46 30 (d, J: 23.54 Hz), 116.33 (d, J: 22.05 Hz), 112.12, 111.79, 35.65 and 35.59 peaks It includes.

137. According to claim 132, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-fluorphenyl)methylidene]acetohydrazide molecule 74 (Formula 2p) electrospray ionization mass spectrum, ESI-HRMS: [M+H]+: It includes peaks m / z 440.0976 and [MH]+: m / z 438.0840.

138. According to claim 132, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-fluorphenyl)methylidene]acetohydrazide molecule (Formula 2p) contains 55.22% C, 4.025% H, and 15.21% N by mass. 5 139. According to claim 132, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-fluorphenyl)methylidene]acetohydrazide molecule (Formula 2p) has a molecular weight of 439.0914 g / mol.

140. A molecule according to claim 11 or 12, whose property is; R1 as "Formula r". If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-10 This involves obtaining [il]sulfanil]-N'-[(4-bromphenyl)methylidene]acetohydrazidine (Formula 2r).

141. According to claim 140, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-bromphenyl)methylidene]acetohydrazide molecule (Formula 2r) means the melting point is 120-122°C.

142. According to claim 140, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-15 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-bromphenyl)methylidene]acetohydrazide molecule (Formula 2r) FTIR spectrum, FTIR ν (cm-1): 3178 cm-1 (NH stretching band), 3079 cm-1 (ar CH stretching band), 2961, 2925 cm-1 (aldehyde CH asymmetric and symmetrical stretching band), 1671 cm-1 (amide C=O stretching band), 1615 cm-1 (hydrazone C=N stretching band), 1509 cm-1 (aromatic C=C stretching, amide II NH 20 bending and CN strain combination bands), 1447, 1381 cm-1 (aldehyde CH asymmetric and symmetric stretch band), 1222 cm-1 (CS stretch band), 1125 cm-1 (aromatic CF stretching band), 842 cm-1 (1,4-disubstituted aromatic CH stretching band) (band) includes peaks.

143. According to claim 140, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-25 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-bromphenyl)methylidene]acetohydrazide molecule (Formula 2r) 1H-NMR spectrum, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.88 and 11.79 (2s, 1H, CONH); 8.23 and 8.04 (2s, 1H, N=CH); 7.83 (d, J: 1.67 Hz, 1H, furan C5-H); 7.71-7.65 (m, 6H, FPhC2,6-H and BrPhC2,3,5,6-H); 7.52 (t, J: 8.69 Hz, 2H, FPhC3,5-H); 6.58 (dd, J: 3.58; 1.67 Hz, 1H, furan C4-H); 6.29 (d, J: 30 It includes peaks of 3.58 Hz, 1H, furan C3-H; 4.52 and 4.13 (2s, 2H, SCH2).

144. According to claim 140, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-bromphenyl)methylidene]acetohydrazide molecule (Formula 2r) 13C-NMR spectrum, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ 75 (ppm): 168.97 and 163.86 (C=O), 163.20 (d, J: 248.78 Hz), 151.88, 147.85, 146.43 and 143.23 (C=N), 145.32, 141.35, 133.64, 132.27, 130.68 (d, J: 9.18 Hz), 130.11 (d, J: 2.76 Hz), 129.18, 123.70, 117.47 (d, J: 23.02 Hz), 112.12, 111.80, 35.66 and It includes peaks of 35.

58.

145. According to claim 140, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-5 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-bromphenyl)methylidene]acetohydrazide molecule (Formula 2r) electrospray ionization mass spectrum, ESI-HRMS: [M+H]+: It includes peaks m / z 502.0178 and [MH]+: m / z 500.0033.

146. According to claim 140, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 10 molecules of 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-bromphenyl)methylidene]acetohydrazide (Formula 2r) contains 49.08% C, 3.468% H, and 13.12% N by mass.

147. According to claim 140, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(4-bromphenyl)methylidene]acetohydrazide molecule (Formula 2r) has a molecular weight of 501.0239 g / mol.

148. A molecule according to claim 11 or 12, whose property is; R1 as "Formula s" 15 If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- [il]sulfanil]-N'-[(2-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2s) It is the process of obtaining it.

149. According to claim 148, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 20 molecules of 1,2,4-triazol-3-yl]sulfanil]-N'-[(2-hydroxyphenyl)methylidene]acetohydrazide (Formula 2s) has a melting point of 191-192.5°C.

150. According to claim 148, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(2-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2s) FTIR spectrum, FTIR ν (cm-1): 3161 cm-1 (NH stretching band), 3010 cm-1 (ar CH stretching band), 2969, 2928, 2853 cm-1 (aldehyde CH asymmetric 25 and symmetrical stretching band), 1672 cm-1 (amid C=O stretching band), 1617 cm-1 (hydrazone C=N stretching band), 1511 cm-1 (aromatic C=C stretching, amide II NH bending and CN strain combination bands), 1453, 1386 cm-1 (aldehyde CH asymmetric and symmetric stretch band), 1225 cm-1 (CS stretch band), 1154 cm-1 (aromatic CF stretching band), 844 cm-1 (1,4-disubstituted aromatic CH stretching 30 (band) includes peaks.

151. According to claim 148, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(2-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2s) 1H-NMR spectrum, 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 76 11.53 and 10.88 (2s, 1H, CONH); 10.01 (s, 1H, OH); 8.34 and 8.23 ​​(2s, 1H, N=CH); 7.69 (d, J: 1.7 Hz, 1H, furan C5-H); 7.57 (dd, 1H, J: 7.67; 1.5 Hz, OHPhC6-H); 7.55-7.52 (m, 2H, FPhC2,6-H); 7.39 (td, J: 8.7; 1.95 Hz, 2H, FPhC3,5-H); 7.22 (td, 1H, J: 7.67; 1.5 Hz, OHPhC4-H); 6.84 (d, 1H, J: 7.67 Hz, OHPhC3-H); 6.78 (t, 1H, J: 7.67 Hz, OHPhC5-H); 6.46 (dd, J: 3.6; 1.8 Hz, 1H, furan C4-H); 6.17 (d, J: 3.7 5 It includes peaks of 4.38 and 3.99 (2s, 2H, SCH2) (Hz, 1H, furan C3-H).

152. According to claim 148, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(2-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2s) 13C-NMR spectrum, 13C-NMR (APT) (125 MHz) (DMSO-d6) δ (ppm): 168.55 and 163.62 (C=O), 163.25 (d, J: 248.75 Hz), 157.78, 151.65, 10 147.96, 147.83 and 141.95 (C=N), 145.36, 141.31, 131.98, 130.69 (d, J: 9.16 Hz), 130.13 (d, J: 2.79 Hz), 129.67, 119.83, 119.05, 117.49 (d, J: 23.01 Hz), 116.83, It includes peaks of 112.14, 111.89, 35.71 and 35.

37.

153. According to claim 148, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(2-hydroxyphenyl)methylidene]acetohydrazide molecule 15 (Formula 2s) electrospray ionization mass spectrum, ESI-HRMS: [M+H]+: It includes peaks m / z 438.1018 and [MH]+: m / z 436.0883.

154. According to claim 148, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(2-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2s) contains 57.12% C, 3.932% H, and 15.81% N by mass. 20 155. According to claim 148, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanil]-N'-[(2-hydroxyphenyl)methylidene]acetohydrazide molecule (Formula 2s) has a molecular weight of 437.0957 g / mol.

156. A molecule according to claim 11 or 12, whose property is; R1 as "Formula t". If selected, 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-25 [il]sulfanil]-N'-[(4-dimethylaminophenyl)methylidene]acetohydrazide molecule (Formula 2t) is the obtaining of.

157. According to claim 156, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-dimethylaminophenyl)methylidene]acetohydrazide The melting point of the molecule (Formula 2t) is 257-258.5°C. 30 158. According to claim 156, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-dimethylaminophenyl)methylidene]acetohydrazide The FTIR spectrum of the molecule (Formula 2t) has an FTIR ν (cm-1): 3161 cm-1 (NH3). (stretch band), 3074 cm-1 (ar CH stretch band), 2895 cm-1 (aldehyde CH 77 asymmetric and symmetrical stretching band), 1666 cm-1 (amide C=O stretching band), 1607 cm-1 (hydrazone C=N stretching band), 1510 cm-1 (aromatic C=C stretching, amide II N- H bending and CN stretching combination bands), 1445, 1384 cm-1 (aldehyde CH (asymmetric and symmetric stretch band) 1221 cm-1 (CS stretch band), 1151 cm-1 (aromatic CF stretching band), 844 cm-1 (1,4-disubstituted aromatic CH stretching 5 (band) includes peaks.

159. According to claim 156, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-dimethylaminophenyl)methylidene]acetohydrazide 1H-NMR spectrum of molecule (Formula 2t), 1H-NMR (500 MHz) (DMSO-d6) δ (ppm): 11.44 and 11.39 (2s, 1H, CONH); 8.03 and 7.87 (2s, 1H, N=CH); 7.78 (d, 10 J: 1.7 Hz, 1H, furan C5-H); 7.63-7.59 (m, 2H, FPhC2,6-H); 7.51-7.44 (m, 6H, FPhC3,5-H and N(CH3)2PhC2,3,5,6-H); 6.54 (dd, J: 3.5; 1.7 Hz, 1H, furan C4-H); 6.24 (d, J: 3.5 Hz, 1H, furan C3-H); 4.43 and 4.03 (2s, 2H, SCH2), 2.97 (s, 6H, -N(CH3)2) It includes its peaks.

160. According to claim 156, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-15 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-dimethylaminophenyl)methylidene]acetohydrazide The 13C-NMR spectrum of the molecule (Formula 2t) is shown in 13C-NMR (APT) (125 MHz) format. (DMSO-d6) δ (ppm): 168.26 and 162.97 (C=O), 163.20 (d, J: 248.36 Hz), 152.03, 151.88, 148.41 and 145.18 (C=N), 147.82, 145.32, 141.43, 130.71 (d, J: 9.23 Hz), 130.18 (d, J: 2.78 Hz), 128.62, 121.68, 117.45 (d, J: 22.96 Hz), 112.22, 112.13, 20 It includes peaks of 111.83, 40.20, 35.76 and 35.

73.

161. According to claim 156, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-dimethylaminophenyl)methylidene]acetohydrazide The electrospray ionization mass spectrum of the molecule (Formula 2t) is shown in ESI. HRMS: [M+H]+: includes peaks m / z 465.1515 and [MH]+: m / z 463.1369. 25 162. According to claim 156, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-dimethylaminophenyl)methylidene]acetohydrazide The molecule (Formula 2t) contains 59.40% C, 4.771% H, and 18.04% N by mass.

163. According to claim 156, it is a molecule with the property of; 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 1,2,4-triazol-3-yl]sulfanyl]-N'-[(4-dimethylaminophenyl)methylidene]acetohydrazide 30 The molecular mass of the molecule (Formula 2t) is 464.1430 g / mol.

164. 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4- with the structure shown by formula 1 The synthesis method of the compound [triazol-3-yl]sulfanil]acetohydrazide is characterized by its; 78 Formula 1 i. 0.03 mol of furan-2-carbohydrazidine solution in absolute ethanol is mixed with 0.03 Addition of 4-fluorophenyl isothiocyanate and reversing in a water bath 5 Heating under a cooler for 1-4 hours, the resulting precipitate will be ready after 1 day. After filtration and drying, N-(4-fluorophenyl)-2-(furan-2- Preparation of carbonyl)hydrazine-1-carbothiamide (Reaction i), ii. N-(4-fluorophenyl)-2-(furan-2-carbonyl)hydrazine-1-carbotioamide 2N 10 in sodium hydroxide (NaOH) under recirculating condenser for 2-4 hours heating and the resulting 4-(4-fluorophenyl)-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4- Precipitation of triazole-3-thion with 12.5% ​​hydrochloric acid (HCl) and Afterwards, the precipitated product is washed with distilled water and dried. as a result 4-(4-Fluorophenyl)-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3- Obtaining thion (Reaction II), 15 iii. 0.005 mol 4-(4-fluorophenyl)-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3- 0.005 mol potassium carbonate (K2CO3) to the suspension of thion in ethanol and the addition of 0.0055 mol of ethyl bromoacetate and reversing in a water bath. After heating under a cooler for 5-6 hours, the reaction medium becomes icy. Pouring it into water and leaving it in the refrigerator for 1 day 20 Subsequently, precipitated ethyl ((4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazole-3- ethyl ((4-fluorophenyl)- as a result of filtration and drying of (1l)sulfanil)acetate Obtaining 5-(furan-2-yl)-4H-1,2,4-triazol-3-yl)sulfanyl)acetate (Reaction iii), iv. 0.005 mol ethyl ((4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazole-3-25 (i)sulfanil)acetate and 1.37 ml hydrazine hydrate starting from 0.028 mol Heating for 5-6 hours under a recirculating cooler in an ethanol environment. As a result, the subject of the invention is 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol- 79 Preparation of the molecule 3-yl]sulfanil]acetohydrazide (Formula 1) (Reaction) iv) It includes the steps of the process.

165. The structure represented by the formula 2a-t is 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H- 5 of the derivatives of 1,2,4-triazol-3-yl]sulfanil]-N'-[(substituted phenyl)methylidene]acetohydrazide It is a synthesis method and its characteristic is; i. 0.03 mol of furan-2-carbohydrazidine solution in absolute ethanol is mixed with 0.03 Addition of 4-fluorophenyl isothiocyanate and reversing in a water bath. Heating under a cooler for 1-4 hours, filtering the resulting precipitate after 1 day. 10 and as a result of drying, N-(4-fluorophenyl)-2-(furan-2-carbonyl)hydrazine-1- Preparation of carbothioamide (Reaction i), ii. N-(4-fluorophenyl)-2-(furan-2-carbonyl)hydrazine-1-carbotioamide 2N sodium heating in hydroxide (NaOH) under a recirculating condenser for 1-4 hours and the resulting 4-(4-fluorophenyl)-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-15 Precipitation of thion with 12.5% ​​hydrochloric acid (HCl) and subsequent precipitation Washing the product with distilled water and drying it results in 4-(4-Fluorophenyl)- Preparation of 5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-thion (Reaction) ii), iii. 0.015 mol 4-(4-fluorophenyl)-5-(furan-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thion 20 0.005 mol of potassium carbonate (K2CO3) was added to its suspension in ethanol. Addition of 0.0055 mol ethyl bromoacetate and reversal in a water bath. After heating under a cooler for 5-6 hours, the reaction contents become ice water. poured into it and left in the refrigerator for 1 day. 80 precipitated ethyl ((4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazole-3- ethyl ((4-fluorophenyl)-5- as a result of filtration and drying of (il)sulfanil)acetate Obtaining (furan-2-yl)-4H-1,2,4-triazol-3-yl)sulfanyl)acetate (Reaction iii), iv. 0.005 mol ethyl ((4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazole-3- Starting from 1.37 ml of 1 / 2 sulfanil acetate and 1 / 37 ml of hydrazine hydrate (0.028 mol), 5 After being heated for 5-6 hours under a recirculating cooler in an ethanolic environment The subject of the invention is 2-[[4-(4-Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3- Preparation of [il]sulfanil]acetohydrazide molecule (Formula 1) (Reaction iv), v. 0.003 mol 2-[[4-(4-fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazole-3- 0.003 mol 10 to the solution of [il]sulfanil]acetohydrazidine (Formula 1) in absolute ethanol addition of aromatic aldehyde compound and water to the reaction mixture boiled in a cooling bath for 5-6 hours and then cooling, filtering out the precipitated hydrazide-hydrazones, and boiling. Purified by washing with ethanol, the subject of the invention is 2-[[4-(4- Fluorophenyl)-5-(furan-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl]-N'-[(substituted 15 phenyl)methylidene]acetohydrazide derivatives in different reaction flasks (2a-t) obtaining It includes the steps of the process.

166. To be used in the treatment of cancer, any of the items in Order 1-163. According to a molecule. 20 167. A drug according to Request 166 for use in the treatment of breast cancer. molecule.

168. A pharmaceutical containing a molecule according to any of claims 1-163. composition.

169. A pharmaceutical according to Claim 168 for use in cancer treatment. 25 composition.

170. A drug according to Request 169 for use in the treatment of breast cancer. pharmaceutical composition.

171. An anti-cancer drug containing a pharmaceutical composition according to claim 168. An effective medicine. 30 172. A molecule as an active ingredient according to any of claims 1-163. a medicine containing.

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