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N-succinic acid mono-substituted indole (azole) spliced podophyllotoxin compound as well as preparation method and application thereof

A technology of podophyllotoxin and succinate, applied in the field of chemistry, can solve the problems of narrow anti-tumor spectrum, disorder, multi-drug resistance gastrointestinal function, etc.

Pending Publication Date: 2022-02-25
遵义医药高等专科学校
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, etoposide (VP-16) and teniposide (VM-26) have become widely used anticancer drugs in clinical practice. It has the disadvantages of narrow anti-tumor spectrum, poor water solubility, multi-drug resistance and serious gastrointestinal dysfunction.

Method used

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  • N-succinic acid mono-substituted indole (azole) spliced podophyllotoxin compound as well as preparation method and application thereof
  • N-succinic acid mono-substituted indole (azole) spliced podophyllotoxin compound as well as preparation method and application thereof
  • N-succinic acid mono-substituted indole (azole) spliced podophyllotoxin compound as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0026] Embodiments of the present invention: 205.0mg indole 1a (1.75mmol), 297.5mg succinic anhydride (1.7eq, 2.975mmol), 21.5mg catalyst 4-dimethylaminopyridine (10%), 0.8 ml triethylamine and 5ml dichloromethane solution, reflux reaction for 12 hours, TLC detected that the reaction was basically complete, spin the solvent, add 40ml ethyl acetate to dilute, then add 1M hydrochloric acid solution, ethyl acetate repeated extraction, combined ethyl acetate layer , and the solvent was spin-dried and purified by silica gel column chromatography (eluent: V (petroleum ether): V (ethyl acetate) = 3:1 to 1:1) to obtain intermediate compound 2a. Take the above intermediate 2a (1.2mmol), 414.41mg podophyllotoxin (1mmol), 24.5mg catalyst 4-dimethylaminopyridine, 309.5mg dehydrating agent N,N'-dicyclohexylcarbodiimide, 8ml dichloromethane The solution was placed in the reaction tube and reacted for 2 hours. TLC detected that the reaction was basically complete. Add 50ml of dichloromethane...

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Abstract

The invention discloses an N-succinic acid mono-substituted indole (azole) spliced podophyllotoxin compound, which simultaneously contains podophyllotoxin and an indole (azole) skeleton, has potential biological activity, provides a compound source for biological activity screening, has important application value for drug screening and pharmaceutical industry, in-vitro anti-tumor activity screening finds that the compounds have a very good inhibition effect on human non-small cell lung cancer cells (A549) and human breast cancer cells (MCF-7), and part of the compounds also have a very good inhibition effect on human lung adenocarcinoma cis-platinum-resistant strains (A549 / DDP), and are superior to positive control drug etoposide; and the compound can be further developed into a novel medicine for preventing and treating tumors. The operation method is very economical, simple and convenient, the product yield is higher, the solubility is better, the raw materials are cheap and easy to obtain, and the antitumor activity of the compound can be further researched and explored.

Description

technical field [0001] The invention relates to the field of chemical technology, in particular to an N-succinic acid monosubstituted indole (azole)-spliced ​​podophyllotoxin compound and its preparation method and application. Background technique [0002] Cancer has become one of the major public health problems that seriously threaten the health of the Chinese population. In recent years, the incidence and death of malignant tumors have continued to rise, and the annual medical expenses caused by malignant tumors exceed 220 billion. Among the 185 countries or regions in the world, the incidence and death of malignant tumors in China are at the upper-middle level. The incidence and death of some digestive tract tumors such as esophageal cancer, gastric cancer, liver cancer and other malignant tumors account for about half of the global total. The overall prevention and control The situation is grim. Podophyllotoxin (Podophyllotoxin) is an aryl naphthalene lignan with sign...

Claims

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Application Information

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IPC IPC(8): C07D493/04C07D519/00A61P35/00
CPCC07D493/04C07D519/00A61P35/00
Inventor 杨俊梁光平黄远梅刘雄利
Owner 遵义医药高等专科学校
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