3-(4-((4-chlorophenoxy)methyl)bicyclo[2.2.2]octan-1-yl)-4-methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazole | 1304515-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-((4-chlorophenoxy)methyl)bicyclo[2.2.2]octan-1-yl)-4-methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazole
• 英文别名: 3-[4-[(4-chlorophenoxy)methyl]-1-bicyclo[2.2.2]octanyl]-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole
• CAS: 1304515-66-9
• 化学式: C₂₅H₂₅ClF₃N₃O
• 分子量: 475.941
• InChiKey: UVDHSOZENUAPIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(4-甲基-5-(2-(三氟甲基)苯基)-4H-1,2,4-噻唑-3-基)双环[2.2.2]辛烷-1-羧酸 在 硼烷 、 caesium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-(4-((4-chlorophenoxy)methyl)bicyclo[2.2.2]octan-1-yl)-4-methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazole
  参考文献：
  名称：

  Bicyclo[2.2.2]octyltriazole inhibitors of 11β-hydoxysteroid dehydrogenase type 1. Pharmacological agents for the treatment of metabolic syndrome

  摘要：

  Following the discovery of a metabolic 'soft-spot' on a bicyclo[2.2.2]octyltriazole lead, an extensive effort was undertaken to block the oxidative metabolism and improve PK of this potent HSD1 lead. In this communication, SAR survey focusing on various alkyl chain replacements will be detailed. This effort culminated in the discovery of a potent ethyl sulfone inhibitor with an improved PK profile across species and improved physical properties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.018

文献信息

• Bicyclo[2.2.2]octyltriazole inhibitors of 11β-hydoxysteroid dehydrogenase type 1. Pharmacological agents for the treatment of metabolic syndrome
  作者：Milana Maletic、Aaron Leeman、Michael Szymonifka、Steven S. Mundt、Hratch J. Zokian、Kashmira Shah、Jasminka Dragovic、Kathy Lyons、Rolf Thieringer、Anne H. Vosatka、James Balkovec、Sherman T. Waddell

  DOI：10.1016/j.bmcl.2011.01.018

  日期：2011.4

  Following the discovery of a metabolic 'soft-spot' on a bicyclo[2.2.2]octyltriazole lead, an extensive effort was undertaken to block the oxidative metabolism and improve PK of this potent HSD1 lead. In this communication, SAR survey focusing on various alkyl chain replacements will be detailed. This effort culminated in the discovery of a potent ethyl sulfone inhibitor with an improved PK profile across species and improved physical properties. (C) 2011 Elsevier Ltd. All rights reserved.