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2-aminobenzimidazoles and applications thereof

A compound, benzo technology, applied in the field of structure with anti-tumor activity, can solve problems such as poor selectivity, toxicity and side effects

Inactive Publication Date: 2013-12-18
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the existing anti-tumor drugs have problems such as poor selectivity, toxic side effects, and drug resistance.

Method used

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  • 2-aminobenzimidazoles and applications thereof
  • 2-aminobenzimidazoles and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 1H-Benzo[d]imidazol-2-amine (1a)

[0041] Add 20ml of water, 5ml of acetonitrile and 0.70g (6.5mmol) of o-phenylenediamine into a 50ml reaction flask, stir evenly and slowly add 0.69g (6.5mmol) of BrCN in batches, heat up to 100°C after addition, reflux for 2h, TLC shows There is no remaining raw material, stop the reaction, adjust the pH to alkaline with ammonia water after cooling, precipitate white and deep, filter with suction, extract the filtrate with ethyl acetate (80ml×3), and use anhydrous MgSO for the organic phase 4 Dry, filter and concentrate under reduced pressure, combine with the filter cake, and recrystallize from ethanol to obtain 0.70 g of white crystals, yield 81.0%, mp.223~226°C, MS[M+H] + 134.05.

Embodiment 2

[0043] 5-Nitro-1H-benzo[d]imidazol-2-amine (1b)

[0044] The preparation method is similar to that of 1a, light red solid, yield 45.5%, mp.212~214°C.

Embodiment 3

[0046]2-Amino-1H-benzo[d]imidazole-5-carboxylic acid ethyl ester (1c)

[0047] The preparation method is similar to that of 1a, white solid, yield 62.9%, mp.216~218℃, MS[M+H] + 206.08.

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PUM

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Abstract

The invention relates to the field of medicinal chemistry and particularly relates to 2-aminobenzimidazoles, preparation methods thereof, medicinal compositions with the 2-aminobenzimidazoles and medical applications of the 2-aminobenzimidazoles.

Description

technical field [0001] The invention relates to the field of medicinal chemistry and provides a class of structures with antitumor activity. Background technique [0002] With the advancement of medicine, general infectious diseases have been gradually controlled, while malignant tumors have become one of the major diseases that are increasingly common and seriously threaten human life and quality of life. According to the World Health Organization, cancer is the leading cause of death worldwide. Of the 58 million deaths worldwide in 2005, 7.6 million (about 13%) died of cancer. , in the next few decades, it is expected that the number of cancer deaths worldwide will continue to increase, with 8.5 million deaths from cancer in 2015 and 14.5 million in 2030. [0003] Antineoplastic drugs refer to drugs against malignant tumors, also known as anticancer drugs. Since nitrogen mustard was used to treat malignant lymphoma in the 1940s, chemotherapy has made great progress in t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/30A61K31/4184A61K31/5377A61K31/454A61P35/00A61P35/02
Inventor 卢帅孙善亮刘海春张亮陆涛
Owner CHINA PHARM UNIV
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