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1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole compound and application thereof

A thiadiazole and triazolo technology is applied in the field of anticancer drugs and achieves the effects of simple process, strong anticancer activity and easy implementation

Inactive Publication Date: 2017-06-20
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no literature report on the relevant anticancer effects of these ten compounds

Method used

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  • 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole compound and application thereof
  • 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole compound and application thereof
  • 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 3-Phenyl-6-n-butyldithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole, the preparation steps are as follows:

[0024] 1) In a 100ml round-bottomed flask, add 12.21g (80.0mmmol) of methyl benzoate (80.0mmmol) and 30ml (excess) of hydrazine hydrate in sequence, and reflux at 80°C for 5h. After the reaction is complete, cool at low temperature to precipitate a solid, suction filter, and dry to obtain benzene Formic hydrazide.

[0025] 2) Take 6.15g (44.0mmol) of benzohydrazide and 3.12g (53.6mmol) of potassium hydroxide and dissolve them in 50ml of absolute ethanol with stirring at room temperature, drop 3ml (0.005mol) of carbon disulfide at 5°C, and immediately produce a white precipitate. Continue to react for 4 hours, filter with suction, and reflux with hydrazine hydrate (35ml, 85wt%) at 80°C for 6 hours. Recrystallize with absolute ethanol to obtain 3-phenyl-4-amino-5-mercapto-1,2,4-triazole.

[0026] 3) Take 2.03g (0.015mol) of 3-phenyl-4-amino-5-mercapto-1,2,4-triazole...

Embodiment 2

[0030] 3-Phenyl-6-isobutyldithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole, the preparation steps are as follows:

[0031] 1) In a 100ml round-bottomed flask, add 12.21g (80.0mmmol) of methyl benzoate (80.0mmmol) and 30ml (excess) of hydrazine hydrate in sequence, and reflux at 80°C for 5h. After the reaction is complete, cool at low temperature to precipitate a solid, suction filter, and dry to obtain benzene Formic hydrazide.

[0032] 2) Take 6.15g (44.0mmol) of benzohydrazide and 3.12g (53.6mmol) of potassium hydroxide and dissolve them in 50ml of absolute ethanol with stirring at room temperature, drop 3ml (0.005mol) of carbon disulfide at 5°C, and immediately produce a white precipitate. Continue to react for 4 hours, filter with suction, and reflux with hydrazine hydrate (35ml, 85wt%) at 80°C for 6 hours. Recrystallize with absolute ethanol to obtain 3-phenyl-4-amino-5-mercapto-1,2,4-triazole.

[0033] 3) Take 2.03g (0.015mol) of 3-phenyl-4-amino-5-mercapto-1,2,4-triazol...

Embodiment 3

[0037] 3-p-methoxyphenyl-6-n-butyldithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole, the preparation steps are as follows:

[0038] 1) In a 100ml round bottom flask, add 14.64g (80.0mmmol) of methyl p-methoxybenzoate (80.0mmmol) and 30ml of hydrazine hydrate (excess) and reflux at 80°C for 5h. After the reaction is complete, cool at low temperature to precipitate a solid, filter and dry That is, p-methoxybenzohydrazide.

[0039] 2) Take 8.05g (44.0mmol) of p-methoxybenzoyl hydrazide and 3.12g (53.6mmol) of potassium hydroxide and dissolve them in 50ml of absolute ethanol with stirring at room temperature, add 3ml (0.005mol) of carbon disulfide dropwise at 5°C, immediately Produce white precipitate, continue to react for 4h, filter with suction, and then reflux with hydrazine hydrate (35ml, 85wt%) at 80°C for 6h, pour into 150ml of ice water after the reaction is complete, adjust the pH value to 3-4 with concentrated hydrochloric acid, and generate a large amount of precipitate ,...

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Abstract

The invention discloses a group of 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole compounds, and application thereof, namely application of ten 3-substituted phenyl-6-butyl dithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole compounds comprising 3-phenyl-6-n-butyl dithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole, 3-phenyl-6-isobutyl dithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole, 3-p-methoxyphenyl-6-n-butyl dithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole and the like. The ten compounds have antitumor activity, are used for preparing drugs for fighting against cervical cancer (Hela), liver cancer (SMMC-7721) and lung cancer (A549), and create a new way for developing a new cancer-fighting drug.

Description

technical field [0001] The invention relates to the field of anticancer drugs, especially 3-substituted phenyl-6-butyldithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole compounds and their applications. Background technique [0002] Cancer is a general term for a large class of malignant tumors, which seriously threaten human health. At present, there are many kinds of anticancer drugs, especially the compounds with triazole or thiadiazole as the parent structure, which have shown good anticancer activity in previous studies and reports. In the middle of the 20th century, people fused triazole and thiadiazole into one molecule for the first time. Since then, many fused ring compounds of triazolothiadiazole have been synthesized with a wide range of biological activities. The latest research shows that these compounds have anti-inflammatory, bactericidal, vasodilation and anti-Alzheimer's effects. New triazolothiadiazole derivatives can be synthesized by modifying the 3-positi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04A61P35/00
CPCC07D513/04
Inventor 陈宝泉刘晓佳唐睿张帅王海欣刘海颖
Owner TIANJIN UNIVERSITY OF TECHNOLOGY