Benzimidazole derivative and preparation method and application thereof

A technology of benzimidazole and derivatives, applied in the field of medicine, to achieve both prevention and treatment, stable quality, and effective oral injection

Active Publication Date: 2018-09-28
ACADEMY OF MILITARY MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, despite decades of efforts by many institutions at home and abroad, some effective radiation protection drugs have been found, but there are still many shortcomings in practice, and there is still a gap between ideal radiation protection drugs

Method used

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  • Benzimidazole derivative and preparation method and application thereof
  • Benzimidazole derivative and preparation method and application thereof
  • Benzimidazole derivative and preparation method and application thereof

Examples

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preparation example Construction

[0061] The present invention also provides a preparation method of the compound of general formula I, adding the compound of formula II and the compound of formula III into the solvent at a molar ratio of 1:1.05, adding the basic catalyst according to the molar ratio of the compound of formula II and the basic catalyst of 1:0.7, and reacting at room temperature After 10 minutes, evaporate to dryness and recrystallize with ethanol to obtain the compound of formula IV. The compound of formula IV and the oxidizing agent are subjected to oxidation reaction at a molar ratio of 1:0.7 for 1 h at a reaction temperature of -10-0° C., and then separated and purified by column chromatography to obtain the compound of formula I. The solvent is selected from dichloromethane, N,N-dimethylformamide, a mixed solvent of dichloromethane and N,N-dimethylformamide; the basic catalyst is selected from sodium hydroxide, potassium hydroxide, ammonia, oxidation Calcium and its aqueous solution, triet...

example 1

[0066] Example 1: Synthesis of 5-chloro-2-mercapto-1-methylbenzimidazole (a1)

[0067] Put 310mg (2mmol) of 2-amino-4-chloro-N-methylaniline and 804mg (5mmol) of potassium ethyl xanthate into a 10mL microwave tube, add 2mL of DMF, stir to completely dissolve, then put into the microwave, Under the conditions of 160psi, 45w, and 165°C, the reaction was complete in 3 minutes to obtain a red clear solution, which was diluted with 30mL of water, adjusted to pH 3-4 with acetic acid, and a milky white solid was precipitated. It was filtered under reduced pressure to obtain 261 mg of off-white solid, which was recrystallized from ethanol to obtain 197 mg of white flocculent solid with a yield of 50.1%. mp 239.5-241°C; 1 H NMR (400MHz, DMSO-d 6 )δ12.87(s,1H), 7.39(d,J=8.4Hz,1H),7.25(d,J=8.4Hz,1H),7.19(s,1H),3.64(s,3H).

example 2

[0068] Example 2: Synthesis of 5-fluoro-2-mercapto-1-methylbenzimidazole (a2)

[0069] According to the preparation method of a1, 397 mg of white floc was obtained from 2-amino-4-fluoro-N-methylaniline and potassium ethyl xanthate, with a yield of 64.1%. mp 239-240°C. 1 H NMR (400MHz, DMSO-d 6 )δ12.85(s,1H), 7.40–7.36(m,1H),7.13–6.98(m,2H),3.64(s,3H).

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Abstract

The invention discloses a benzimidazole derivative and a preparation method and application thereof. The structure of the benzimidazole derivative is as shown in the general formula I in the specification. The benzimidazole derivative has characteristics of high efficiency and low toxicity, prevention and treatment, stable quality, convenience in use, effectiveness in both oral administration andinjection and the like, can directly confront multi-system injuries caused by radiation, and effectively alleviate symptoms of acute radiation sickness to save precious time for subsequent comprehensive treatment. The invention provides a new thinking and direction for the development of a safe and highly-efficient radioprotector.

Description

technical field [0001] The invention relates to the field of medical technology, in particular to a benzimidazole derivative capable of preventing and treating radiation damage, a preparation method and application thereof. Background technique [0002] The prevention and treatment of radiation injury caused by nuclear radiation has always been a major medical issue of great concern at home and abroad. Radiation protection drugs, namely radiation injury prevention drugs and / or radiation injury treatment drugs, can directly combat multi-system damage caused by radiation, effectively alleviate the symptoms of acute radiation sickness, and win valuable opportunities for follow-up comprehensive treatment. Therefore, it is of great practical significance to develop efficient and safe radiation protection drugs. [0003] In the field of radiation protection drugs (that is, radiation damage prevention drugs and / or radiation damage treatment drugs), great progress has been made a...

Claims

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Application Information

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IPC IPC(8): C07D235/28A61K31/4184A61P39/00
CPCC07D235/28
Inventor 张首国王林周玉美唐林彭涛王刚温晓雪杨建云黄荣清孙云波刘曙晨
Owner ACADEMY OF MILITARY MEDICAL SCI
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