4-bromo-5-(2-chloro-benzoylamino)-(1-(2-N,N-dimethylamino)ethyl)-pyrazole-3-carboxylic acid [2-(3,4,5,6-tetrahydro-2H-[1,4']bipyridin-4-yl)-ethyl]-amide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-5-(2-chloro-benzoylamino)-(1-(2-N,N-dimethylamino)ethyl)-pyrazole-3-carboxylic acid [2-(3,4,5,6-tetrahydro-2H-[1,4']bipyridin-4-yl)-ethyl]-amide
• 英文别名: 4-bromo-5-[(2-chlorobenzoyl)amino]-1-[2-(dimethylamino)ethyl]-N-[2-(1-pyridin-4-ylpiperidin-4-yl)ethyl]pyrazole-3-carboxamide
• 化学式: C₂₇H₃₃BrClN₇O₂
• 分子量: 602.962
• InChiKey: AWYVOTLFOBPIEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl)ethylamine 、 在 N-甲基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-bromo-5-(2-chloro-benzoylamino)-(1-(2-N,N-dimethylamino)ethyl)-pyrazole-3-carboxylic acid [2-(3,4,5,6-tetrahydro-2H-[1,4']bipyridin-4-yl)-ethyl]-amide
  参考文献：
  名称：

  Preparation and Optimization of a Series of 3-Carboxamido-5-phenacylaminopyrazole Bradykinin B1 Receptor Antagonists

  摘要：

  The B1 receptor is an attractive target for the treatment of pain and inflammation. A series of 3-carboxamido5-phenacylamino pyrazole B1 receptor antagonists are described that exhibit good potency against B1 and high selectivity over B2. Initially, N-unsubstituted pyrazoles were studied, but these compounds suffered from extensive glucuronidation in primates. This difficulty could be surmounted by the use of N-substituted pyrazoles. Optimization efforts culminated in compound 41, which has high receptor potency and metabolic stability.

  DOI：

  10.1021/jm051292n