Benzimidazole derivative, preparation method thereof and application of benzimidazole derivative to tumor resistance

A technology of benzimidazoles and derivatives, which is applied in its preparation method and its application in anti-tumor. In the field of benzimidazole derivatives, it can solve the problems of limited application and limited types of topoisomerase inhibitors.

Active Publication Date: 2018-02-16
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the types of topoisomerase inhibitors are l

Method used

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  • Benzimidazole derivative, preparation method thereof and application of benzimidazole derivative to tumor resistance
  • Benzimidazole derivative, preparation method thereof and application of benzimidazole derivative to tumor resistance
  • Benzimidazole derivative, preparation method thereof and application of benzimidazole derivative to tumor resistance

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preparation example Construction

[0063] The present invention also provides a kind of preparation method of benzimidazole derivatives, comprising the following steps:

[0064] performing a first condensation reaction on rhodanine or its derivatives with a first compound having a structure represented by formula (II), to obtain a benzimidazole derivative having a structure represented by formula (I);

[0065]

[0066] Among them, R 1 and R 2 Independently selected from one of hydrogen, halogen, alkyl, alkoxy, haloalkyl, nitro and nitrile; preferably independently selected from hydrogen, halogen, alkyl with 1 to 5 carbon atoms, carbon atoms One of an alkoxy group with a number of 1 to 5, a haloalkyl group with a carbon number of 1 to 5, a nitro group, and a nitrile group; more preferably independently selected from hydrogen, chlorine, fluorine, bromine, iodine, and methoxy One of , methyl, trifluoromethyl, nitro and nitrile;

[0067] R 3 is carboxyl, alkyl, phenyl or cyano; preferably carboxyl, alkyl wit...

Embodiment 1

[0112] Synthesis of compounds A2, b2, c2, d2, e2, f2, g2, h2, i2, j2, k2

[0113] The molar ratio of 1:1.5 o-phenylenediamine or its derivatives and glycolic acid was catalyzed by 4N hydrochloric acid, and reacted at 100°C for 6h. After the reaction, cool to room temperature, adjust the pH to 8 with sodium bicarbonate solution, precipitate a solid, filter it with suction, and dry it by infrared.

[0114]

Embodiment 2

[0116] Synthesis of Compounds A3~A22

[0117] Benzyl bromide with a molar ratio of 1:1 and compound A2 were dissolved in DMF, and a potassium carbonate solid with a molar ratio of benzyl bromide of 1:5 was reacted at room temperature for 8 h. After the reaction, extract with ethyl acetate and water, collect the organic phase, and purify with a silica gel column to obtain a white solid with a yield of 80-93%.

[0118]

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Abstract

The invention provides a benzimidazole derivative which is provided with a structure as shown in a formula (I). R1 and R2 are independently selected from one of hydrogen, halogen, alkyl, alkoxy, halogenated alkyl, nitryl and a nitrile group, R3 is carboxyl, alkyl, phenyl or a cyano group, the value range of m is 0-3, the value range of n is 0-3, X is CH or nitrogen, and Y is CH2 or carbonyl. The benzimidazole derivative has a strong inhibiting effect on activity of topoisomerase II, so that the benzimidazole derivative can serve as a topoisomerase II inhibitor. Research finds that the compoundis the catalytic inhibitor of Topo II, so that the compound can be used for preparing an anti-tumor drug taking the topoisomerase II as a target spot. Besides, the benzimidazole derivative has good anti-proliferative activity for a plurality of tumor cells, so that the benzimidazole derivative can be used for preparing the anti-tumor drug.

Description

technical field [0001] The invention relates to the fields of medicine and chemical industry, in particular to a benzimidazole derivative, its preparation method and its application in antitumor. Background technique [0002] Cancer seriously threatens human health and life safety. According to statistics, about 4 million people around the world are diagnosed with cancer every year. In China, 8,500 new cancer patients are added every day, and one in eight people dies of cancer. Therefore, the research and development of anti-tumor drugs has always been a hot spot in current scientific research, and anti-tumor drugs with high efficiency and low toxicity are one of the important directions of research and development. [0003] Topoisomerase plays an important role in the process of DNA replication, transcription and repair. In tumor cells, topoisomerases are overexpressed. If the activity of topoisomerase is inhibited, it will cause the disorder of cellular nucleic acid me...

Claims

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Application Information

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IPC IPC(8): C07D417/06A61K31/427A61P35/00
CPCC07D417/06
Inventor 杜志云黎鹏辉江宏张文进招敏聪陈惠雄董长治郑希张焜
Owner GUANGDONG UNIV OF TECH
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