5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(2-ethylbutanoyl)-N,4-dimethyl-1H-pyrazole-3-carboxamide | 1159836-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(2-ethylbutanoyl)-N,4-dimethyl-1H-pyrazole-3-carboxamide
• 英文别名: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(2-ethylbutanoyl)-N,4-dimethylpyrazole-3-carboxamide
• CAS: 1159836-22-2
• 化学式: C₂₄H₂₄Cl₃N₃O₂
• 分子量: 492.832
• InChiKey: VIMREJGUAHNEIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-n,4-dimethyl-1H-pyrazole-3-carboxamide 、 2-乙基丁酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(2-ethylbutanoyl)-N,4-dimethyl-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis and structure–activity relationship of novel diarylpyrazole imide analogues as CB1 cannabinoid receptor ligands

  摘要：

  A myriad of research groups have been engaged in searching for novel CB1 receptor antagonists, since SR141716A (rimonabant), a CB1 receptor antagonist, was discovered for an obesity treatment. In this research, extended series, based on the 1,5-diarylpyrazole template of rimonabant, was synthesized and tested for CB1 receptor binding affinity. In the present study, N-piperidinylcarboxamide group of rimonabant was replaced with the corresponding sulfonamide, imide, N-methylimide and methylenediamide, respectively. The SAR studies to optimize the CB1 binding affinity led to the potent imide derivatives. The in vivo efficacy test of a derivative (16f) gave a promising result for this novel scaffold. In order to explore physicochemical properties (hydrophobic, steric and electronic) of the representative imide derivatives responsible for their CB1 receptor binding affinity, quantitative structure activity relationship (QSAR) studies were performed. Hansch QSAR models, which were moderate in the explanation for SAR, were generated with hydrophobic, steric and electronic properties of substituents. Especially, the Taft Es-based parabolic model was obtained with the best correlation result (r(2) = 0.846). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.006