N-cyclopropyl-4-fluorocyclohexan-1-amine | 917865-88-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: N-cyclopropyl-4-fluorocyclohexan-1-amine
• CAS: 917865-88-4
• 化学式: C₉H₁₆FN
• 分子量: 157.231
• InChiKey: YARCNPWHTRSITD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-(1,1,1-trifluoro-2-hydroxypropan-2-yl) benzoic acid 、 N-cyclopropyl-4-fluorocyclohexan-1-amine 在 碳酸氢钠 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以10%的产率得到(S)-N-(trans-4-fluorocyclohexyl)-4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)-N-cyclopropylbenzamide
  参考文献：
  名称：

  Discovery of Novel, Potent Benzamide Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1) Exhibiting Oral Activity in an Enzyme Inhibition ex Vivo Model^▽

  摘要：

  We report the discovery of potent benzamide inhibitors of 11beta-hydroxysteroid dehydrogenase (11beta-HSD1). The optimization and correlation of in vitro and in vivo metabolic stability will be described. Through modifications to our initial lead 2, we discovered pyridyl compound 13. This compound has a favorable pharmacokinetic profile across three species and showed a dose-dependent decrease in adipose 11beta-HSD1 activity in a monkey ex vivo pharmacodynamic model.

  DOI：

  10.1021/jm800310g
• 作为产物：
  描述：

  4-氟环己酮 、 环丙胺 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 N-cyclopropyl-4-fluorocyclohexan-1-amine
  参考文献：
  名称：

  Discovery of Novel, Potent Benzamide Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1) Exhibiting Oral Activity in an Enzyme Inhibition ex Vivo Model^▽

  摘要：

  We report the discovery of potent benzamide inhibitors of 11beta-hydroxysteroid dehydrogenase (11beta-HSD1). The optimization and correlation of in vitro and in vivo metabolic stability will be described. Through modifications to our initial lead 2, we discovered pyridyl compound 13. This compound has a favorable pharmacokinetic profile across three species and showed a dose-dependent decrease in adipose 11beta-HSD1 activity in a monkey ex vivo pharmacodynamic model.

  DOI：

  10.1021/jm800310g

文献信息

• BENZAMIDE DERIVATIVES AND USES RELATED THERETO
  申请人：Amgen Inc.

  公开号：EP1904435B1

  公开（公告）日：2013-01-02
• US7605289B2
  申请人：——

  公开号：US7605289B2

  公开（公告）日：2009-10-20
• US8637576B2
  申请人：——

  公开号：US8637576B2

  公开（公告）日：2014-01-28
• Discovery of Novel, Potent Benzamide Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1) Exhibiting Oral Activity in an Enzyme Inhibition ex Vivo Model^▽
  作者：Lisa D. Julian、Zhulun Wang、Tracy Bostick、Seb Caille、Rebekah Choi、Michael DeGraffenreid、Yongmei Di、Xiao He、Randall W. Hungate、Juan C. Jaen、Jinsong Liu、Mario Monshouwer、Dustin McMinn、Yosup Rew、Athena Sudom、Daqing Sun、Hua Tu、Stefania Ursu、Nigel Walker、Xuelei Yan、Qiuping Ye、Jay P. Powers

  DOI：10.1021/jm800310g

  日期：2008.7

  We report the discovery of potent benzamide inhibitors of 11beta-hydroxysteroid dehydrogenase (11beta-HSD1). The optimization and correlation of in vitro and in vivo metabolic stability will be described. Through modifications to our initial lead 2, we discovered pyridyl compound 13. This compound has a favorable pharmacokinetic profile across three species and showed a dose-dependent decrease in adipose 11beta-HSD1 activity in a monkey ex vivo pharmacodynamic model.