2,2-dicyclohexyl-N-{(3aS,4S,6aR)-2-[3-(trifluoromethoxy)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}acetamide | 1228024-60-9

• 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: 2,2-dicyclohexyl-N-{(3aS,4S,6aR)-2-[3-(trifluoromethoxy)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}acetamide
• 英文别名: N-[(3aS,4S,6aR)-2-[[3-(trifluoromethoxy)phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide
• CAS: 1228024-60-9
• 化学式: C₂₉H₄₁F₃N₂O₂
• 分子量: 506.652
• InChiKey: PGPJDRQJYRXXAU-DMDYGQEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二环己基乙酸 在 20 % Pd(OH)2/C 、 氢气 、 1-羟基苯并三唑 、 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 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 反应 52.0h， 生成 2,2-dicyclohexyl-N-{(3aS,4S,6aR)-2-[3-(trifluoromethoxy)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}acetamide
  参考文献：
  名称：

  Synthesis and SAR of 4-aminocyclopentapyrrolidines as N-type Ca2+ channel blockers with analgesic activity

  摘要：

  A novel 4-aminocyclopentapyrrolidine series of N-type Ca2+ channel blockers have been discovered. Enantioselective synthesis of the 4-aminocyclopentapyrrolidines was enabled using N-tert-butyl sulfinamide chemistry. SAR studies demonstrate selectivity over L-type Ca2+ channels. N-type Ca2+ channel blockade was confirmed using electrophysiological recording techniques. Compound 25 is an N-type Ca2+ channel blocker that produces antinociception in inflammatory and nociceptive pain models without exhibiting cardiovascular or motor liabilities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.057

文献信息

• NOVEL SUBSTITUTED OCTAHYDROCYCLOPENTA[C]PYRROL-4-AMINES AS CALCIUM CHANNEL BLOCKERS
  申请人：Stewart Andrew O.

  公开号：US20100130558A1

  公开（公告）日：2010-05-27

  The present application relates to calcium channel inhibitors containing compounds of formula (I) wherein L 1 , L 2 , R 1 , R 2 , and R 3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本申请涉及含有式（I）化合物的钙通道抑制剂，其中L1、L2、R1、R2和R3如规范中所定义。本申请还涉及包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• US8129417B2
  申请人：——

  公开号：US8129417B2

  公开（公告）日：2012-03-06
• [EN] NOVEL SUBSTITUTED OCTAHYDROCYCLOPENTA [C]PYRROL-4-AMINES AS CALCIUM CHANNEL BLOCKERS<br/>[FR] NOUVELLES OCTAHYDROCYCLOPENTA[C]PYRROL-4-AMINES SUBSTITUÉES COMME BLOQUEURS DE CANAUX CALCIQUES
  申请人：ABBOTT LAB

  公开号：WO2011149995A1

  公开（公告）日：2011-12-01

  The present application relates to calcium channel inhibitors containing compounds of formula (I) wherein L1, L2, R1, R2, and R3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.
• Synthesis and SAR of 4-aminocyclopentapyrrolidines as N-type Ca2+ channel blockers with analgesic activity
  作者：Xenia Beebe、Daria Darczak、Rodger F. Henry、Timothy Vortherms、Richard Janis、Marian Namovic、Diana Donnelly-Roberts、Karen L. Kage、Carol Surowy、Ivan Milicic、Wende Niforatos、Andrew Swensen、Kennan C. Marsh、Jill M. Wetter、Pamela Franklin、Scott Baker、Chengmin Zhong、Gricelda Simler、Erica Gomez、Janel M. Boyce-Rustay、Chang Z. Zhu、Andrew O. Stewart、Michael F. Jarvis、Victoria E. Scott

  DOI：10.1016/j.bmc.2012.04.057

  日期：2012.7

  A novel 4-aminocyclopentapyrrolidine series of N-type Ca2+ channel blockers have been discovered. Enantioselective synthesis of the 4-aminocyclopentapyrrolidines was enabled using N-tert-butyl sulfinamide chemistry. SAR studies demonstrate selectivity over L-type Ca2+ channels. N-type Ca2+ channel blockade was confirmed using electrophysiological recording techniques. Compound 25 is an N-type Ca2+ channel blocker that produces antinociception in inflammatory and nociceptive pain models without exhibiting cardiovascular or motor liabilities. (C) 2012 Elsevier Ltd. All rights reserved.