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Application of O-(benzimidazolyl) ethyl derivative of cleistanthus sumatranus ketone in preparation of drug for curing or preventing renal fibrosis

A technology of benzimidazolyl and ethyl derivatives, which is applied in drug combinations, medical preparations containing active ingredients, organic chemistry, etc., can solve the problems of low safety and high toxicity, and achieve good anti-renal fibrosis Effect

Inactive Publication Date: 2015-08-19
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 renal fibrosis 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 O-(benzimidazolyl) ethyl derivative of cleistanthus sumatranus ketone in preparation of drug for curing or preventing renal fibrosis
  • Application of O-(benzimidazolyl) ethyl derivative of cleistanthus sumatranus ketone in preparation of drug for curing or preventing renal fibrosis
  • Application of O-(benzimidazolyl) ethyl derivative of cleistanthus sumatranus ketone in preparation of drug for curing or preventing renal fibrosis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Preparation of Compound Cleistanone

[0018] The preparation method of the compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. , pages 4108–4111, August 2011).

[0019]

Embodiment 2

[0020] Example 2 Synthesis of O-Bromoethyl Derivatives (II) of Cleistanone

[0021] Compound I (440 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and tetrabutylammonium bromide (TBAB) (0.04 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 25 °C for 24 h. After 24 hours, the reaction solution was poured into ice water, extracted twice with dichloromethane immediately, and the organic phase solutions were combined. Then the organic phase solution was washed with water and saturated brine three times successively, then dried with anhydrous sodium sulfate, and finally 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, v / v), and the yellow concentrated elution band was collected to obtain compound II as a yellow solid (344 mg, 63%).

[0022] 1H NMR (500 MHz, DMSO-d ...

Embodiment 3

[0026] Example 3 Synthesis of O-(benzimidazolyl)ethyl derivative (III) of cleistanone Cleistanone

[0027] 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 thereto, and the mixture was heated to reflux for 5h . After the reaction was completed, the reaction solution was poured into ice water, extracted three times with an equal amount of dichloromethane, and the organic phases were combined. The combined organic phases were successively washed with water and saturated brine, 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), and the concentrated brown elution band was collected and concentrated to give compound III as a brown solid (105.2 m...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry, in particular to an O-(benzimidazolyl) ethyl derivative of Cleistanone, a preparation method and application of the O-(benzimidazolyl) ethyl derivative in preparation of drug for curing or preventing renal fibrosis. A new O-(benzimidazolyl) ethyl derivative of Cleistanone is synthesized, and the preparation method is disclosed. Pharmacological experiments show that the O-(benzimidazolyl) ethyl derivative has effect on preventing or curing renal fibrosis and has value in developing the drug for preventing or curing renal fibrosis.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to O-(benzimidazolyl)ethyl derivatives of cleistanone, a preparation method and uses thereof. Background technique [0002] Renal fibrosis (including renal interstitial fibrosis and glomerulosclerosis) is the main pathological basis of the final stage of renal damage caused by various reasons. Proliferation and activation of stromal cells are related to the imbalance of vasoactive substances, cytokines and extracellular matrix transformation. Renal interstitial fibrosis is almost a common path for all primary or secondary renal diseases to progress to end-stage renal failure. It is urgent to develop anti-renal fibrosis drugs with high efficiency and low toxicity. [0003] The existing drugs for the treatment of renal fibrosis have the problems of high toxicity and low safety. It is of great value to find compounds or lead compounds from natural products and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/58A61P13/12C07J63/00
Inventor 江春平黄蓉
Owner NANJING GUANGKANGXIE BIOLOGICAL MEDICAL TECH
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