1-(2,4-dichlorophenyl)-4-methyl-N-(octan-2-yl)-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamide | 1262121-94-7

• 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-dichlorophenyl)-4-methyl-N-(octan-2-yl)-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamide
• 英文别名: 1-(2,4-dichlorophenyl)-4-methyl-N-octan-2-yl-5-pyrrol-1-ylpyrazole-3-carboxamide
• CAS: 1262121-94-7
• 化学式: C₂₃H₂₈Cl₂N₄O
• 分子量: 447.408
• InChiKey: DOQRGXMYBKLLBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  30
• 可旋转键数：
  9
• 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：
  2

反应信息

• 作为产物：
  描述：

  (±)-4-氨基辛烷 、 1-(2,4-二氯苯基)-4-甲基-5-(1H-吡咯-1-y)-1H-吡唑-3-羧酸 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70%的产率得到1-(2,4-dichlorophenyl)-4-methyl-N-(octan-2-yl)-5-(1H-pyrrol-1-yl)-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