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N-cyclopropane substituent-containing curcumin analogue and drug application thereof

A technology of curcumin analogs and propane, which is applied in the field of curcumin analogs and can solve problems such as side effects and affecting the treatment effect of patients

Inactive Publication Date: 2016-04-20
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, at present, there are certain side effects of steroidal and non-steroidal anti-inflammatory drugs used in the treatment or prevention of bacterial-induced sepsis and chemical-induced inflammatory reactions, which affect the therapeutic effect of patients.

Method used

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  • N-cyclopropane substituent-containing curcumin analogue and drug application thereof
  • N-cyclopropane substituent-containing curcumin analogue and drug application thereof
  • N-cyclopropane substituent-containing curcumin analogue and drug application thereof

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Embodiment Construction

[0016] refer to figure 1 , the molecular expression of the present invention containing the curcumin analogue that N-cyclopropane replaces is:

[0017] (3E,5E)-3-(3-allyl-4-hydroxybenzylidene)-1-cyclopropyl-5-(2,4-dimethoxybenzylidene)piperidine-4 - a ketone, (abbreviated as S8 in the following text).

[0018] The spectral data of the compound are as follows: yellow solid, the yield is 25%, and the melting point is 182.6°C-184.5°C; 1 H-NMR (600MH Z ,DMSO-d 6 ): δ=10.03(1H,s,Ar-OH),7.79(1H,s,H-β'),7.49(1H,s,H-β),7.24(1H,d,J=6.0Hz,H -6'),7.23(1H,d,J=7.8Hz,H-6),7.22(1H,s,H-2),6.69(1H,s,H-3'),6.92(1H,d, J=7.8Hz, H-5), 6.64 (1H, d, J=6.0Hz, H-5'), 6.02-5.95 (1H, m, A-ArCH 2 CH=CH 2 ),5.09-5.04(2H,m,A-ArCH 2 CH=CH 2 ),3.89(2H,s,A-ArCH 2 CH=CH 2 ),3.85(4H,s,piperidone-CH 2 -N-CH 2 ),3.83(6H,s,2',4'-OCH 3 ),1.97-1.94(1H,m,-N-CH-Cyclopropyl),0.45-0.42(2H,m,N-CH 2 -CH 2 -Cyclopropyl),0.26-0.23(2H,m,N-CH 2 -CH 2 -Cyclopropyl); 13 C-NMR (600MH Z ,DMSO-d 6 ):δ=186.07,1...

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Abstract

The invention discloses an N-cyclopropane substituent-containing curcumin analogue. The molecular expression of the curcumin analogue is (3E,5E)-3-(3-allyl-4-hydroxyl benzylidene)-1-cyclopropyl-5-(2,4-dimethoxy benzylidene)piperidine-4-ketone. The invention further discloses drug application of the N-cyclopropane substituent-containing curcumin analogue. The N-cyclopropane substituent-containing curcumin analogue is applied to prevention or treatment of sepses induced by bacteria and inflammatory reactions induced by chemical substances, wherein the sepses induced by the bacteria comprise inflammatory factor release induced by lipopolysaccharide (LPS) and septic death induced by the LPS, and the inflammatory reactions induced by the chemical substances comprise ear swelling induced by xylene, vascular permeability increasing caused by intraperitoneal injection of acetic acid and twisting number increasing caused by acetic acid.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical preparations, relates to a curcumin analog containing N-cyclopropane substitution, and also relates to a drug for treating or preventing sepsis induced by bacteria and inflammation induced by chemical substances by the curcumin analog application. Background technique [0002] Inflammation refers to various damaging changes in cells and tissues when exogenous and endogenous injury factors act on the body. At the same time, a series of complex reactions also occur locally and throughout the body to limit and eliminate injury factors, eliminate And this comprehensive body defense response that absorbs dead tissue and cells, and repairs the damage. Inflammatory response mediates the occurrence and development of various diseases and plays an important role in the progression of diseases. The inflammatory response is mostly manifested as the release of a large amount of pro-inflammatory facto...

Claims

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Application Information

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IPC IPC(8): C07D213/68A61K31/451A61P31/04A61P29/00A61P27/16A61P9/14A61P43/00
CPCC07D213/68
Inventor 陈通克王丽花汤陌生
Owner WENZHOU MEDICAL UNIV
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