(1S,2R)-2-[(1R)-1-aminoprop-2-ynyl]-N,N-diethyl-1-phenylcyclopropane-1-carboxamide | 779308-86-0

• 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: (1S,2R)-2-[(1R)-1-aminoprop-2-ynyl]-N,N-diethyl-1-phenylcyclopropane-1-carboxamide
• CAS: 779308-86-0
• 化学式: C₁₇H₂₂N₂O
• 分子量: 270.374
• InChiKey: KVSRHZKOXHLCCI-YQQAZPJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-[(1R)-1-aminoprop-2-ynyl]-N,N-diethyl-1-phenylcyclopropane-1-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以74%的产率得到(1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide
  参考文献：
  名称：

  Synthesis and Biological Activity of Conformationally Restricted Analogues of Milnacipran:  (1S,2R)-1-Phenyl-2-[(R)-1-amino-2-propynyl]-N,N- diethylcyclopropanecarboxamide Is a Novel Class of NMDA Receptor Channel Blocker

  摘要：

  Conformationally restricted analogues of (+/-)-(Z)-2-aminomethyl-1-phenyl-N, N-diethylcyclopropanecarboxamide [milnacipran, (+/-)-1] were designed on the basis of its characteristic cyclopropane structure and were synthesized enantioselectively to develop efficient NMDA receptor antagonists. Among these analogues, (1S,2R)-1-phenyl-2-[(R)-1-amino-2-propynyl]- N,N-diethylcyclopropanecarboxamide (2d) had one of the most potent affinities for the receptor, with a K-i value of 0.29 mu M. The blockade of NMDA receptor channels expressed by Xenopus oocytes by 2d was investigated in detail, and 2d was identified as a new class of open channel blocker against this receptor.

  DOI：

  10.1021/jm980238m
• 作为产物：
  描述：

  (1S,2R)-2-Formyl-1-phenyl-cyclopropanecarboxylic acid diethylamide 在 吡啶 、 ammonium hydroxide 、 正丁基锂 、 sodium azide 、 四溴化碳 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 41.5h， 生成 (1S,2R)-2-[(1R)-1-aminoprop-2-ynyl]-N,N-diethyl-1-phenylcyclopropane-1-carboxamide
  参考文献：
  名称：

  Synthesis and Biological Activity of Conformationally Restricted Analogues of Milnacipran:  (1S,2R)-1-Phenyl-2-[(R)-1-amino-2-propynyl]-N,N- diethylcyclopropanecarboxamide Is a Novel Class of NMDA Receptor Channel Blocker

  摘要：

  Conformationally restricted analogues of (+/-)-(Z)-2-aminomethyl-1-phenyl-N, N-diethylcyclopropanecarboxamide [milnacipran, (+/-)-1] were designed on the basis of its characteristic cyclopropane structure and were synthesized enantioselectively to develop efficient NMDA receptor antagonists. Among these analogues, (1S,2R)-1-phenyl-2-[(R)-1-amino-2-propynyl]- N,N-diethylcyclopropanecarboxamide (2d) had one of the most potent affinities for the receptor, with a K-i value of 0.29 mu M. The blockade of NMDA receptor channels expressed by Xenopus oocytes by 2d was investigated in detail, and 2d was identified as a new class of open channel blocker against this receptor.

  DOI：

  10.1021/jm980238m