(1S,2S)-2-(aminomethyl)-N,N-diethyl-1-(thiophen-2-yl)cyclopropanecarboxamide | 942576-32-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,2S)-2-(aminomethyl)-N,N-diethyl-1-(thiophen-2-yl)cyclopropanecarboxamide
• 英文别名: (1R,2R)-2-aminomethyl-1-thiophen-2-yl-cyclopropanecarboxylic acid diethylamide；(1R,2R)-2-(aminomethyl)-N,N-diethyl-1-(thiophen-2-yl)cyclopropanecarboxamide；(1R,2R)-2-(aminomethyl)-N,N-diethyl-1-thiophen-2-ylcyclopropane-1-carboxamide
• CAS: 942576-32-1
• 化学式: C₁₃H₂₀N₂OS
• 分子量: 252.381
• InChiKey: LRXREOMAEUNNPU-GWCFXTLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-(aminomethyl)-N,N-diethyl-1-(thiophen-2-yl)cyclopropanecarboxamide 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以30%的产率得到diethyl (1R,2R)-2-aminomethyl-1-(5-chlorothiophen-2-yl)cyclopropanecarboxamide
  参考文献：
  名称：

  WO2007/98356

  摘要：

  公开号：
• 作为产物：
  描述：

  (1R,2R)-2-[(1,3-dioxoisoindol-2-yl)methyl]-N,N-diethyl-1-thiophen-2-ylcyclopropane-1-carboxamide 在 肼 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 (1S,2S)-2-(aminomethyl)-N,N-diethyl-1-(thiophen-2-yl)cyclopropanecarboxamide
  参考文献：
  名称：

  Studies on a series of milnacipran analogs containing a heteroaromatic group as potent norepinephrine and serotonin transporter inhibitors

  摘要：

  A series of milnacipran analogs containing a heteroaromatic group were synthesized and studied as monoamine transporter inhibitors. Many compounds exhibited higher potency than milnacipran at NET and NET/SERT with no significant change in lipophilicity. For example, compound R-26f was about 10-fold more potent than milnacipran with IC(50) values of 8.7 and 26 nM at NET and SERT, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.045

文献信息

• Synthesis of enantiomerically pure milnacipran analogs and inhibition of dopamine, serotonin, and norepinephrine transporters
  作者：Heidi Roggen、Jan Kehler、Tine Bryan Stensbøl、Tore Hansen

  DOI：10.1016/j.bmcl.2007.02.054

  日期：2007.5

  A series of Milnacipran analogs with variation in the aromatic moiety were prepared in high enantionteric excess. Structure-activity relationships for two parallel enantionteric series are described. The (-)-(1R,2S)-naphthyl analog (8h) showed the highest potency in the two series and is a triple reuptake inhibitor of the SERT, NET, and DAT. (c) 2007 Elsevier Ltd. All rights reserved.
• Studies on a series of milnacipran analogs containing a heteroaromatic group as potent norepinephrine and serotonin transporter inhibitors
  作者：Troy Vickers、Brian Dyck、Junko Tamiya、Mingzhu Zhang、Florence Jovic、Jonathan Grey、Beth A. Fleck、Anna Aparicio、Michael Johns、Liping Jin、Hui Tang、Alan C. Foster、Chen Chen

  DOI：10.1016/j.bmcl.2008.04.045

  日期：2008.6

  A series of milnacipran analogs containing a heteroaromatic group were synthesized and studied as monoamine transporter inhibitors. Many compounds exhibited higher potency than milnacipran at NET and NET/SERT with no significant change in lipophilicity. For example, compound R-26f was about 10-fold more potent than milnacipran with IC(50) values of 8.7 and 26 nM at NET and SERT, respectively. (C) 2008 Elsevier Ltd. All rights reserved.
• WO2007/98356
  申请人：——

  公开号：——

  公开（公告）日：——