4,5-di-substituted-phenyl-1,2,3-thiadia-zole derivative, and its preparation method and uses

A technology for thiadiazoles and derivatives, applied in 4 fields, can solve the problems of complex synthesis, poor water solubility, high toxicity and the like

Inactive Publication Date: 2006-11-22
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, CA-4 itself has poor water solubility, and it is easy to form trans isomers and lose its activity. The structural modification reported in the literature has disadvantages such as complicated synthesis, insufficient activity, or high toxicity.

Method used

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  • 4,5-di-substituted-phenyl-1,2,3-thiadia-zole derivative, and its preparation method and uses
  • 4,5-di-substituted-phenyl-1,2,3-thiadia-zole derivative, and its preparation method and uses
  • 4,5-di-substituted-phenyl-1,2,3-thiadia-zole derivative, and its preparation method and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1: Preparation of 4-p-methoxyphenyl-5-(3,4,5-trimethoxyphenyl)-1,2,3-thiadiazole (compound 15) represented by the following structural formula.

[0068]

[0069] Dissolve 2-(3,4,5-trimethoxyphenyl)-1-(4-methoxyphenyl)-ethanone (1mmol) and p-toluenesulfonylhydrazide (2mmol) in ethanol (25ml) , heating to reflux for 3h, distilling off the solvent under reduced pressure, and draining with an oil pump. Dissolve in dry chloroform (30 ml), add thionyl chloride (2 ml) carefully dropwise, cool with ice water, naturally rise to room temperature, and react for 4 hours. Stop the reaction, evaporate the solvent under reduced pressure, add saturated aqueous sodium bicarbonate solution, separate the layers, and extract. The organic phase was washed successively with saturated aqueous sodium bicarbonate solution and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The product was obtained by column separation with a yield of 51%.

[0070]Mp: 9...

Embodiment 2

[0071] Embodiment 2: the preparation of compound 1

[0072] Compound 1 was prepared in the same manner as in Example 1 except that corresponding raw materials were used. The structural formula, melting point, and NMR and MS data of Compound 1 are listed in Table 1 below.

Embodiment 3

[0073] Embodiment 3: the preparation of compound 2

[0074] Compound 2 was prepared in the same manner as in Example 1 except that corresponding raw materials were used. The structural formula, melting point, and NMR and MS data of Compound 2 are listed in Table 1 below.

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Abstract

The invention relates to a 4,5- disubstituted phenyl-1,2,3-thiadiazole deruivatives, and the use of these compounds as microtubule depressor in preparing tumor-resisting medicaments, the invention also relates to the process for preparing the compounds.

Description

technical field [0001] The present invention relates to a 4,5-disubstituted phenyl-1,2,3-thiadiazole derivative, and the application of the compound as a microtubule inhibitor in the preparation of antitumor drugs, and also relates to the preparation of the compound Preparation. Background technique [0002] Tumors, especially malignant tumors, have seriously threatened human health and life safety, and are the number one cause of death in China. Discovering and searching for new and effective anti-tumor drugs is a major issue at present. [0003] Tubulin is an important target for finding anti-tumor drugs. There have been many important microtubule inhibitors that constitute an important part of anti-tumor drugs. Hundreds of microtubule inhibitors, including natural, semi-synthetic or fully Synthetic, has been reported. Among them, Combretastatin A-4 (CA-4), isolated from southern African willow, has a very powerful microtubule inhibitory effect. Due to the simple struc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/06A61K31/433A61P35/00C07D417/04
Inventor 吴茂江丁健陈奕林莉萍杨春皓谢毓元
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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