1-(2,4-difluorophenyl)-5-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(3,3-dimethylbutyl)-4-methyl-1H-pyrazole-3-carboxamide | 1262122-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2,4-difluorophenyl)-5-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(3,3-dimethylbutyl)-4-methyl-1H-pyrazole-3-carboxamide
• 英文别名: 1-(2,4-difluorophenyl)-N-(3,3-dimethylbutyl)-5-(2,5-dimethylpyrrol-1-yl)-4-methylpyrazole-3-carboxamide
• CAS: 1262122-00-8
• 化学式: C₂₃H₂₈F₂N₄O
• 分子量: 414.498
• InChiKey: BDEOVMZDXDAANU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,3-二甲基丁胺 、 1-(2,4-difluorophenyl)-5-(2,5-dimethyl-pyrrol-1-yl)-4-methyl-1H-pyrazole-3-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以89%的产率得到1-(2,4-difluorophenyl)-5-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(3,3-dimethylbutyl)-4-methyl-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of new N-alkyl 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides as cannabinoid receptor ligands

  摘要：

  A series of N-alkyl 1-ary1-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides were synthesized as new ligands of the human recombinant receptor hCB(1). n-Alkyl carboxamides brought out different SARs from the branched subgroup. Unsubstituted pyrrole derivatives bearing a tert-alkyl chain at the 3-carboxamide nitrogen showed greater hCB1 receptor affinity than the corresponding unbranched compounds. In particular, the tert-butyl group as a chain terminal moiety strongly improved hCB(1) receptor affinity (compound 24: K-i; = 45.6 nM; 29: K-i = 37.5 nM). Acute administration of either compound 12 or 29 resulted in a specific, dose-dependent reduction in food intake in rats. Such results provide an useful basis for the design of new CB1 ligands. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.053

文献信息

• Synthesis and biological evaluation of new N-alkyl 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides as cannabinoid receptor ligands
  作者：Romano Silvestri、Alessia Ligresti、Giuseppe La Regina、Francesco Piscitelli、Valerio Gatti、Antonio Lavecchia、Antonella Brizzi、Serena Pasquini、Marco Allarà、Noemi Fantini、Mauro Antonio Maria Carai、Chiara Bigogno、Marco Giulio Rozio、Roberta Sinisi、Ettore Novellino、Giancarlo Colombo、Vincenzo Di Marzo、Giulio Dondio、Federico Corelli

  DOI：10.1016/j.ejmech.2010.09.053

  日期：2010.12

  A series of N-alkyl 1-ary1-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides were synthesized as new ligands of the human recombinant receptor hCB(1). n-Alkyl carboxamides brought out different SARs from the branched subgroup. Unsubstituted pyrrole derivatives bearing a tert-alkyl chain at the 3-carboxamide nitrogen showed greater hCB1 receptor affinity than the corresponding unbranched compounds. In particular, the tert-butyl group as a chain terminal moiety strongly improved hCB(1) receptor affinity (compound 24: K-i; = 45.6 nM; 29: K-i = 37.5 nM). Acute administration of either compound 12 or 29 resulted in a specific, dose-dependent reduction in food intake in rats. Such results provide an useful basis for the design of new CB1 ligands. (C) 2010 Elsevier Masson SAS. All rights reserved.