N'-(4-fluoro-3-trifluoromethyl-phenyl)-N-[4-(3-cyanophenyl)-4-hydroxycyclohexyl]-N-[2-(1-pyrrolidinyl)ethyl]urea | 540781-58-6

• 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: N'-(4-fluoro-3-trifluoromethyl-phenyl)-N-[4-(3-cyanophenyl)-4-hydroxycyclohexyl]-N-[2-(1-pyrrolidinyl)ethyl]urea
• CAS: 540781-58-6
• 化学式: C₂₇H₃₀F₄N₄O₂
• 分子量: 518.554
• InChiKey: BDDQJCMHMSWBAC-HNACLESGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  79.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N'-(4-fluoro-3-trifluoromethyl-phenyl)-N-[4-(3-cyanophenyl)-4-hydroxycyclohexyl]-N-[2-(1-pyrrolidinyl)ethyl]urea 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到1-[4-(3-Cyano-phenyl)-cyclohex-3-enyl]-3-(4-fluoro-3-trifluoromethyl-phenyl)-1-(2-pyrrolidin-1-yl-ethyl)-urea
  参考文献：
  名称：

  Bicyclic[4.1.0]heptanes as phenyl replacements for melanin concentrating hormone receptor antagonists

  摘要：

  Melanin concentrating hormone (MCH) receptor antagonists have been proposed as potential treatments of obesity. MCH receptor antagonists with a biphenylamine subunit have been reported previously at Schering-Plough. Herein, we report the discovery of bicyclo[4.1.0]heptanes as replacements for the middle phenyl ring of the biphenylamine moiety, in order to eliminate its potential mutagenic liability. Structure-activity relationships in this series were found to be very similar to those of the original biphenylamine series, suggesting that the two series have similar binding modes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.046
• 作为产物：
  描述：

  4-(3-cyanophenyl)-4-hydroxycyclohexan-1-one 在 sodium cyanoborohydride 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N'-(4-fluoro-3-trifluoromethyl-phenyl)-N-[4-(3-cyanophenyl)-4-hydroxycyclohexyl]-N-[2-(1-pyrrolidinyl)ethyl]urea
  参考文献：
  名称：

  Bicyclic[4.1.0]heptanes as phenyl replacements for melanin concentrating hormone receptor antagonists

  摘要：

  Melanin concentrating hormone (MCH) receptor antagonists have been proposed as potential treatments of obesity. MCH receptor antagonists with a biphenylamine subunit have been reported previously at Schering-Plough. Herein, we report the discovery of bicyclo[4.1.0]heptanes as replacements for the middle phenyl ring of the biphenylamine moiety, in order to eliminate its potential mutagenic liability. Structure-activity relationships in this series were found to be very similar to those of the original biphenylamine series, suggesting that the two series have similar binding modes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.046

文献信息

• US7348328B2
  申请人：——

  公开号：US7348328B2

  公开（公告）日：2008-03-25