N-(4-bromophenyl)-1-cyclopentylpiperidin-4-amine | 862652-48-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-bromophenyl)-1-cyclopentylpiperidin-4-amine
• CAS: 862652-48-0
• 化学式: C₁₆H₂₃BrN₂
• 分子量: 323.276
• InChiKey: MCVKYYKJGYUAKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-1-cyclopentylpiperidin-4-amine 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-(3-Chloro-4-fluoro-phenyl)-1-(3'-cyano-biphenyl-4-yl)-1-(1-cyclopentyl-piperidin-4-yl)-urea
  参考文献：
  名称：

  Biaryl Ureas as Potent and Orally Efficacious Melanin Concentrating Hormone Receptor 1 Antagonists for the Treatment of Obesity

  摘要：

  Herein, we report a small molecule MCH-R1 antagonist which demonstrates oral efficacy in chronic rodent models. Substituted phenyl biaryl urea derivatives were synthesized and evaluated as MCH-R1 antagonists for the treatment of obesity. The structure-activity relationship studies in this series resulted in identification of urea 1 as a potent and selective MCH-R1 antagonist. Compound I exhibited oral efficacy in chronic (28 d) rodent models at 3-30 mpk showing significant reduction in food intake and weight gain relative to controls.

  DOI：

  10.1021/jm0503852
• 作为产物：
  描述：

  1-Boc-4-(4-溴苯氨基)-哌啶 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 N-(4-bromophenyl)-1-cyclopentylpiperidin-4-amine
  参考文献：
  名称：

  Biaryl Ureas as Potent and Orally Efficacious Melanin Concentrating Hormone Receptor 1 Antagonists for the Treatment of Obesity

  摘要：

  Herein, we report a small molecule MCH-R1 antagonist which demonstrates oral efficacy in chronic rodent models. Substituted phenyl biaryl urea derivatives were synthesized and evaluated as MCH-R1 antagonists for the treatment of obesity. The structure-activity relationship studies in this series resulted in identification of urea 1 as a potent and selective MCH-R1 antagonist. Compound I exhibited oral efficacy in chronic (28 d) rodent models at 3-30 mpk showing significant reduction in food intake and weight gain relative to controls.

  DOI：

  10.1021/jm0503852

文献信息

• Reduction of hERG inhibitory activity in the 4-piperidinyl urea series of H3 antagonists
  作者：Michael Berlin、Yoon Joo Lee、Christopher W. Boyce、Yi Wang、Robert Aslanian、Kevin D. McCormick、Steve Sorota、Shirley M. Williams、Robert E. West、Walter Korfmacher

  DOI：10.1016/j.bmcl.2010.01.121

  日期：2010.4

  Structural features of the substituted 4-piperidinyl urea analogs 1, responsible for the H3 antagonist activity, have been identified. Structure-activity relationship of the H3 receptor affinity, hERG ion channel inhibitory activity and their separation is described. Preliminary pharmacokinetic evaluation of the compounds of the series is addressed. (C) 2010 Elsevier Ltd. All rights reserved.