Application of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs for increasing leukocyte

A technology of benzimidazolyl and ethyl derivatives, which is applied in the field of preparation of O-ethyl derivatives of Cleistanone, which can solve the problems of low safety and high leukocyte toxicity

Inactive Publication Date: 2015-08-12
NANJING GUANGKANGXIE BIOLOGICAL MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The existing drugs for the treatment of leukopenia have the problems of high toxicity and low safety. It is of great value to find compounds or lead compounds from natural products and carry out structural modification to obtain their derivatives, so as to obtain potential drugs with high efficiency and low toxicity

Method used

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  • Application of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs for increasing leukocyte
  • Application of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs for increasing leukocyte
  • Application of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs for increasing leukocyte

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 Preparation of the compound Cleistanone

[0019] The preparation method of the compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. (Van Trinh Thi Thanh et al., 2011.Cleistanone: A Triterpenoid from Cleistanthus indochinensis with a New Carbon Skeleton.Volume 2011, Issue 22 , pages 4108-4111, August 2011) method.

[0020]

[0021]

Embodiment 2

[0022] Example 2 Synthesis of O-bromoethyl derivative (II) of Cleistanone

[0023] Compound I (440mg, 1.00mmol) was dissolved in 10mL of benzene, tetrabutylammonium bromide (TBAB) (0.04g), 1,2-dibromoethane (3.760g, 20.00mmol) and 6mL of benzene were added to the solution 50% sodium hydroxide solution. The mixture was stirred at 25 degrees Celsius for 24 h. After 24h, the reaction solution was poured into ice water, immediately extracted with dichloromethane twice, and the organic phase solutions were combined. Then the organic phase solution was washed three times with water and saturated brine in turn, and then dried over anhydrous sodium sulfate, and finally concentrated under reduced pressure to remove the solvent to obtain the crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1, v / v), and the yellow concentrated elution band was collected to obtain compound II as a yellow solid (344 mg, 63%).

[0024...

Embodiment 3

[0028] Example 3 Synthesis of O-(benzimidazolyl) ethyl derivative (III) of Cleistanone

[0029] Compound II (273mg, 0.5mmol) was dissolved in 15mL of acetonitrile, anhydrous potassium carbonate (345mg, 2.5mmol), potassium iodide (84mg, 0.5mmol) and benzimidazole (1180mg, 10mmol) were added to it, and the mixture was heated to reflux for 5h . After the reaction, the reaction solution was poured into ice water, extracted three times with the same amount of dichloromethane, and the organic phases were combined. The combined organic phase was washed with water and saturated brine in turn, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1.5, v / v), the brown concentrated elution band was collected, and concentrated to obtain the brown solid of compound III (105.2 mg, 36%).

[0030] 1H NMR(500MHz,DMSO-...

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Abstract

The invention relates to the fields of organic synthesis and pharmaceutical chemistry, and specifically relates to a cleistanone O-(benzimidazolyl) ethyl derivative, a preparation method thereof, and an application of the cleistanone O-(benzimidazolyl) ethyl derivative in the preparation of drugs for increasing the leukocyte. A novel cleistanone O-(benzimidazolyl) ethyl derivative is synthesized, and a preparation method thereof is disclosed. The pharmacological experiments show that the cleistanone O-(benzimidazolyl) ethyl derivative has an effect on increasing leukocyte and can be used to develop drugs for increasing leukocyte.

Description

Technical field [0001] The present invention relates to the field of organic synthesis and medicinal chemistry, in particular to the O-(benzimidazolyl) ethyl derivative of Cleistanone, a preparation method and application thereof. Background technique [0002] Leukopenia is a disease caused by unknown causes and secondary to other diseases. It is divided into two categories: primary and secondary. The cause of primary patients is unknown; secondary patients believe that the cause can be acute infection, physical and chemical factors, blood system diseases, diseases with splenomegaly, connective tissue diseases, allergic diseases, genetic diseases, etc., acquired or Unexplained neutropenia, etc. [0003] The treatment of leukopenia The existing drugs have the problems of high toxicity and low safety. It is important to find compounds or lead compounds from natural products and modify their structures to obtain their derivatives, so as to obtain potential drugs with high efficiency ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/58A61P7/00A61P7/06C07J63/00
Inventor 王慧吴俊艺
Owner NANJING GUANGKANGXIE BIOLOGICAL MEDICAL TECH
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