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Medicament of 1,3,4-oxadiazole containing pyrazole compound prepared for treating tumor

A compound, oxadiazole technology, applied in the field of medicinal chemistry, can solve the problem of urgency in the development of anti-tumor drugs, and achieve the effect of inhibiting proliferation

Inactive Publication Date: 2014-08-06
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no treatment or drug that can completely cure tumors so far, so the development of anti-tumor drugs is urgent

Method used

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  • Medicament of 1,3,4-oxadiazole containing pyrazole compound prepared for treating tumor
  • Medicament of 1,3,4-oxadiazole containing pyrazole compound prepared for treating tumor
  • Medicament of 1,3,4-oxadiazole containing pyrazole compound prepared for treating tumor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 5-[3-(4-Methoxyphenyl)-1-arylmethylpyrazol-5-yl]-2-(N-phenylacetamide-2-sulfanyl)-1,3,4- Preparation of oxadiazole (I-1)

[0038]Under an ice-water bath, slowly add 2.07 g (0.09 mol) of sodium to 50 mL of ethanol. After it is completely dissolved, add dropwise a mixed solution of 10.35 mL (0.075 mol) of ethyl oxalate and 30 mL of ethanol at room temperature, and stir evenly. Add 12.69 mL (0.093 mol) of 4-methoxyacetophenone (II-1) dropwise, and drop it for 1.5 h. After stirring for 4 h, filter under reduced pressure, wash with ethanol three times, and dry in vacuo to obtain a light yellow solid Compound 16.32 g.

[0039] Dissolve 1.09 g (4.5 mmol) of the light yellow solid compound in 10 mL of acetic acid, add 0.35 mL (5.6 mmol) of 80% hydrazine hydrate, N 2 Reflux for 4 h under protection, cool to room temperature, pour the reaction solution into an ice-water mixture, precipitate a light yellow solid under stirring, filter under reduced pressure, wash the filter cake...

Embodiment 2

[0052] 5-[3-(4-methoxyphenyl)-1-arylmethylpyrazol-5-yl]-2-(N-(2-chlorophenyl)acetamide-2-thio)-1 , Preparation of 3,4-oxadiazole (I-2)

[0053] Replace aniline (VIII-1) with 2-chloroaniline (VIII-2), follow the method described in Example 1, and all the other required raw materials and reagents are the same as Example 1 to obtain a yellow-white solid 5-[3-(4- Methoxyphenyl)-1-arylmethylpyrazol-5-yl]-2-(N-(2-chlorophenyl)acetamide-2-thio)-1,3,4-oxadiazole , yield 87%.

[0054] Mp: 212-213 °C; 1 H NMR (DMSO- d6 ) δ: 3.77 (s, 3H, OCH 3 ), 4.23~4.37 (m, 2H, SCH 2 CO), 5.70 (s, 2H, CH 2 Ph), 6.98 (t, J = 8.5 Hz, 2H, ArH), 7.17~7.32 (m, 6H, ArH), 7.53 (s, 3H, ArH), 7.67 (d, J = 8.3 Hz, 3H, ArH), 11.04 (s, 1H, NH); ESI-MS m / z: 532.2 [M+H] + , 554.2 [M+Na] + ; IR (KBr, v ): 3433, 3175, 3153, 3064, 2934, 2843, 2359, 2041, 1731, 1654, 1626, 1543, 1515, 1495, 1480, 1449, 1438, 1417, 1368, 13693, 180, 13 1127, 1110, 1064, 1026 cm -1 .

Embodiment 3

[0056] 5-[3-(4-methoxyphenyl)-1-arylmethylpyrazol-5-yl]-2-(N-(4-chlorophenyl)acetamide-2-thio)-1 , Preparation of 3,4-oxadiazole (I-3)

[0057] With 4-chloroaniline (VIII-3) instead of aniline (VIII-1), according to the method described in Example 1, all the other required raw materials and reagents are the same as in Example 1 to obtain a yellow solid 5-[3-(4-methyl Oxyphenyl)-1-arylmethylpyrazol-5-yl]-2-(N-(4-chlorophenyl)acetamide-2-thio)-1,3,4-oxadiazole, Yield 87%.

[0058] Mp: 239-241 °C; 1 H NMR (DMSO- d6 ) δ: 3.78 (s, 3H, OCH 3 ), 4.19 (s, 2H, SCH 2 CO), 5.69 (s, 2H, CH 2 Ph), 6.98 (t, J = 8.6 Hz, 2H, ArH), 7.18~7.33 (m, 6H, ArH), 7.40 (d, J = 8.5 Hz, 2H, ArH), 7.59 (d, J = 8.5 Hz, 2H, ArH), 7.68 (d, J = 8.4 Hz, 2H, ArH), 11.02 (s, 1H, NH); ESI-MS m / z: 532.2 [M+H] + , 554.2 [M+Na] + ; IR (KBr, v ): 3445, 3179, 3067, 3002, 2932, 2837, 2560, 2300, 2035, 1961, 1896, 1728, 1652, 1616, 1537, 1507, 1487, 1434, 1363, 1337, 14, 129 1089, 1024, 953, 897 cm ...

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Abstract

The invention discloses a medicament of a 1,3,4-oxadiazole containing pyrazole compound prepared for treating tumor, which comprises 1,3,4-oxadiazole containing pyrazole compound, and a pharmaceutical acceptable salt thereof as shown in the formula (I), wherein in the formula (1), R1, R2 and R3 refer to H, halogen, C1-C6 alkyls, aryl, C1-C4 alkoxys or nitryls; n refers to 1, 2, 3, or 4; and the halogen is fluorine, chlorine, bromine or iodine. The compound or pharmaceutical acceptable salt thereof is an acid added salt formed by the compound shown in the formula (I) and the following acids: a hydrochloric acid, a sulfuric acid, a benzenesulfonic acid or a p-toluenesulfonic acid. The medicament comprises a solvate of the compound shown in the formula (I) and water, ethanol, ethyl ether or acetone. The medicament has an inhibitory effect on human liver cancer cells. The compound shown in the formula (I) is a drug which can be used for preventing and treating related diseases such as various abnormal cell proliferation and morphologic changes and the like, and especially used for treating and preventing tumor diseases.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a pyrazole compound containing 1,3,4-oxadiazole, its preparation method and its medical use, especially in the preparation of drugs for treating or preventing tumors. Background technique [0002] With the accelerated pace of modern life and increasingly serious environmental pollution, the incidence of tumors has increased rapidly, and has become the number one killer of human health in some developed countries. Although human beings have been struggling with tumor diseases for hundreds of years, and have discovered a variety of methods and drugs for treating tumor diseases. However, there is no treatment or drug that can completely cure tumors so far, so the research and development of anti-tumor drugs is urgent. [0003] In the field of antitumor drug research, pyrazole compounds are a research hotspot. Pyrazoles refer to a class of simple aromatic heterocyclic organic com...

Claims

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Application Information

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IPC IPC(8): C07D413/04A61K31/4245A61P35/00
CPCC07D413/04
Inventor 王京张磊姚其正
Owner ZUNYI MEDICAL UNIVERSITY
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