(S)-2-methyl-N-((3aR,4R,6aS)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-yl)propane-2-sulfinamide | 1384106-81-3

• 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: (S)-2-methyl-N-((3aR,4R,6aS)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-yl)propane-2-sulfinamide
• CAS: 1384106-81-3
• 化学式: C₁₉H₂₇F₃N₂OS
• 分子量: 388.497
• InChiKey: SEIJZHSLBMTIAC-QBDNARRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  32.34
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-2-methyl-N-((3aR,4R,6aS)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-yl)propane-2-sulfinamide 在 盐酸 、 水 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以88%的产率得到(3aR,4R,6aS)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine
  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
• 作为产物：
  描述：

  (S,E)-2-methyl-N-((3aR,6aS)-2-(3-(trifluoromethyl)benzyl)hexahydrocyclopenta[c]pyrrol-4(5H)-ylidene)propane-2-sulfinamide 在 sodium tetrahydroborate 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以73%的产率得到(S)-2-methyl-N-((3aR,4R,6aS)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-yl)propane-2-sulfinamide
  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