[3-[(1S)-1-(dimethylamino)ethyl]phenyl] N-[(2S)-1-phenylpropan-2-yl]carbamate;hydrochloride | 1247027-68-4

• 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: [3-[(1S)-1-(dimethylamino)ethyl]phenyl] N-[(2S)-1-phenylpropan-2-yl]carbamate;hydrochloride
• CAS: 1247027-68-4
• 化学式: C₂₀H₂₆N₂O₂*ClH
• 分子量: 362.9
• InChiKey: NYCWANXMIHRYBR-MOGJOVFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  41.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3-[(1S)-1-(dimethylamino)ethyl]phenyl] N-[(2S)-1-phenylpropan-2-yl]carbamate;hydrochloride 在 recombinant human acetylcholinesterase 作用下， 生成 二氧化碳 、 右旋苯丙胺 、 3-(1-(S)-(N,N-二甲基氨基)乙基)苯酚
  参考文献：
  名称：

  Novel carbamate cholinesterase inhibitors that release biologically active amines following enzyme inhibition

  摘要：

  Conjugation of the phenol derived from rivastigmine with amphetamines gave access to novel carbamate cholinesterase inhibitors. All compounds possessed increased affinity and selectivity for AChE compared to rivastigmine and were orally bioavailable. Compound 4a, incorporating d-amphetamine, caused significant inhibition of cholinesterase in vivo at doses that were well tolerated. Release of amphetamine from 4a was demonstrated following in vitro and in vivo inhibition of cholinesterase. Compound 4a was also effective in alleviating scopolamine induced amnesia in a rat passive avoidance model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.089
• 作为产物：
  描述：

  s-riva-d-amphetamine 在 盐酸 作用下， 以 乙醚 为溶剂， 以100%的产率得到[3-[(1S)-1-(dimethylamino)ethyl]phenyl] N-[(2S)-1-phenylpropan-2-yl]carbamate;hydrochloride
  参考文献：
  名称：

  COMPOSITIONS OF CHOLINESTERASE INHIBITORS

  摘要：

  本发明涉及与3-((S)-1-(二甲基氨基)乙基)苯基甲基-((R)-1-苯基丙烷-2基)氨基甲酸酯及其药用可接受盐形式相关的合成的组合物、使用方法和过程，包括富马酸盐。本发明还涉及3-((S)-1-(二甲基氨基)乙基)苯基甲基-((R)-1-苯基丙烷-2基)氨基甲酸酯的新型形态多晶形态，其具有独特的X射线衍射图案和差示扫描量热分析剖面，以及独特的晶体结构。

  公开号：

  US20100256229A1

文献信息

• COMPOSITIONS OF CHOLINESTERASE INHIBITORS
  申请人：Du Shoucheng

  公开号：US20100256229A1

  公开（公告）日：2010-10-07

  The present invention is directed to compositions, methods of use, and processes for the synthesis related to 3-((S)-1-(dimethylamino)ethyl)phenyl methyl-((R)-1-phenylpropan-2 yl)carbamate, and its pharmaceutically acceptable salt forms, including the hydrogen fumarate salt. The present invention also relates to a novel form polymorph of 3-((S)-1-(dimethylamino)ethyl)phenylmethyl-((R)-1-phenylpropan-2 yl)carbamate, characterized by a unique X-ray diffraction pattern and Differential Scanning Calorimetry profile, as well a unique crystalline structure.

  本发明涉及与3-((S)-1-(二甲基氨基)乙基)苯基甲基-((R)-1-苯基丙烷-2基)氨基甲酸酯及其药用可接受盐形式相关的合成的组合物、使用方法和过程，包括富马酸盐。本发明还涉及3-((S)-1-(二甲基氨基)乙基)苯基甲基-((R)-1-苯基丙烷-2基)氨基甲酸酯的新型形态多晶形态，其具有独特的X射线衍射图案和差示扫描量热分析剖面，以及独特的晶体结构。
• Novel carbamate cholinesterase inhibitors that release biologically active amines following enzyme inhibition
  作者：Jeroen C. Verheijen、Kjesten A. Wiig、Shoucheng Du、Stacie L. Connors、Ashley N. Martin、Jennifer P. Ferreira、Vladimir I. Slepnev、Ulrike Kochendörfer

  DOI：10.1016/j.bmcl.2009.04.089

  日期：2009.6

  Conjugation of the phenol derived from rivastigmine with amphetamines gave access to novel carbamate cholinesterase inhibitors. All compounds possessed increased affinity and selectivity for AChE compared to rivastigmine and were orally bioavailable. Compound 4a, incorporating d-amphetamine, caused significant inhibition of cholinesterase in vivo at doses that were well tolerated. Release of amphetamine from 4a was demonstrated following in vitro and in vivo inhibition of cholinesterase. Compound 4a was also effective in alleviating scopolamine induced amnesia in a rat passive avoidance model. (C) 2009 Elsevier Ltd. All rights reserved.