Acridine-1,2,4-triazole-5-thioketone compound and preparation method and applications of acridine-1,2,4-triazole-5-thioketone compound

A technology of compound and acridine, which is applied in the field of medicine, can solve problems that have not been seen before, and achieve the effects of improving binding ability, increasing conjugation area, and significant in vitro anti-tumor activity

Active Publication Date: 2015-01-14
广西新桂环保科技集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, there are no related reports on the introduction of aromatic heterocyclic structures

Method used

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  • Acridine-1,2,4-triazole-5-thioketone compound and preparation method and applications of acridine-1,2,4-triazole-5-thioketone compound
  • Acridine-1,2,4-triazole-5-thioketone compound and preparation method and applications of acridine-1,2,4-triazole-5-thioketone compound
  • Acridine-1,2,4-triazole-5-thioketone compound and preparation method and applications of acridine-1,2,4-triazole-5-thioketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation method of 4-(2-methoxyacridinyl)-3-p-nitrophenyl-1,2,4-triazole-5-thione, the specific steps are as follows:

[0030] 1) In a 250ml three-necked flask, add 5.20g (26mmol) of o-bromobenzoic acid (26mmol), p-methoxyaniline (34mmol), 7.5g (36.2mmol) of potassium carbonate and 0.3g (4.7mmol) of copper powder, and then add 30ml Isoamyl alcohol was used as a solvent, refluxed and stirred at 140°C for 2 hours; after the reaction, the solvent was evaporated under reduced pressure, and the obtained residue was added with 600ml of water, reacted at 80°C for 20min, filtered while hot, washed the filter cake, combined the water layer, and used the water layer Concentrated hydrochloric acid was acidified to PH2, and a large amount of light green precipitate was precipitated, which was filtered by suction, and the obtained solid was recrystallized with chloroform to obtain compound 1 with a yield of 79%;

[0031] 2) In a 100ml round bottom flask, add 14.38g (18mmol) o...

Embodiment 2

[0039] Repeat Example 1, the difference is:

[0040] In step 1), change the consumption of potassium carbonate to 5.39g (26mmol), copper powder 0.17g (2.6mmol), replace isoamyl alcohol with n-amyl alcohol, change the temperature during reflux to 150°C, and combine the water The layer was acidified to pH=1 with concentrated hydrochloric acid;

[0041] In step 3), the consumption of sodium thiocyanate is changed to 1.62g (20mmoL), the temperature during reaction is changed to 70°C, and the organic solvent acetone is replaced with methanol;

[0042] In step 4), methanol is used to replace the organic solvent absolute ethanol, and the temperature during reflux is changed to 70°C;

[0043] In step 5), the amount of sodium carbonate was changed to 3g, and it was added to the reaction system in the form of 20w / w% sodium carbonate aqueous solution.

[0044] The separated pale yellow solid was analyzed by mass spectrometry and carbon spectrometry, and it was determined to be 4-(2-met...

Embodiment 3

[0046] Repeat Example 1, the difference is:

[0047] In step 1), the temperature at reflux was changed to 160° C., and the combined aqueous layer was acidified to pH=3 with concentrated hydrochloric acid;

[0048] In step 3), replace organic solvent acetone wherein with acetonitrile;

[0049] In step 4), change the consumption of p-nitrobenzohydrazide to 0.72g (4mmol), replace the organic solvent wherein with the composition of methanol and ethanol (the volume ratio of methanol and ethanol is 5:1) ethanol.

[0050] The separated pale yellow solid was analyzed by mass spectrometry and carbon spectrometry, and it was determined to be 4-(2-methoxyacridinyl)-3-p-nitrophenyl-1,2,4-triazole-5-thione .

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Abstract

The invention discloses an acridine-1,2,4-triazole-5-thioketone compound and a preparation method and applications of the acridine-1,2,4-triazole-5-thioketone compound. The preparation method of the compound comprises the following steps: 1) by taking an o-bromobenzoic acid and p-methoxyaniline as raw materials, taking potassium carbonate and copper powder as catalysts, and taking isopentyl alcohol or n-amyl alcohol as a solvent, reacting so as to obtain a compound 1; 2) carrying out cyclization on the compound 1 by using phosphorus oxychloride so as to obtain a compound 2; 3) after the compound 2 is dissolved by using an organic solvent, in the presence of tetrabutylammonium bromide, reacting the dissolved compound 2 with sodium sulfocyanate so as to obtain a compound 3; 4) after the compound 3 is dissolved by using an organic solvent, reacting the dissolved compound 3 with m-nitrobenzoylhydrazine so as to obtain a compound 4; and 5) reacting the compound 4 with sodium carbonate, carrying out suction filtration on a reactant, collecting filter liquor, adjusting the pH value of the filter liquor to be less than 4, separating out precipitates, and carrying out suction filtration on the precipitates. In-vitro antitumor test results show that the compound has a significant in-vitro antitumor activity to tested MGC80-3, NCI-H460 and T24.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to an acridine-1,2,4-triazole-5-thione compound and a preparation method and application thereof. Background technique [0002] Studies have shown that malignant tumors are one of the stubborn diseases that seriously endanger human life today. According to reports, the cancer mortality rate is about 1 / 4 of the world's diseases, ranking second, only after cardiovascular diseases. Due to the serious harm and high mortality of malignant tumors, the prevention and treatment of cancer has become the focus of people's attention. [0003] DNA is an ideal biological target in the development of anti-tumor drugs, and DNA intercalators can be better embedded in the middle of DNA base pairs in the double helix, which provides a basis for the design of DNA-targeted anti-tumor drugs. Chromophore molecules with a planar rigid structure often play an important role in the design and in vitro scr...

Claims

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Application Information

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IPC IPC(8): C07D401/04A61K31/473A61P35/00
CPCC07D401/04
Inventor 刘华钢霍丽妮
Owner 广西新桂环保科技集团有限公司
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