(R)-tert-Butoxycarbonylamino-((1R,2S)-2-diethylcarbamoyl-2-phenyl-cyclopropyl)-acetic acid methyl ester | 213018-89-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-tert-Butoxycarbonylamino-((1R,2S)-2-diethylcarbamoyl-2-phenyl-cyclopropyl)-acetic acid methyl ester
• 英文别名: methyl (2R)-2-[(1R,2S)-2-(diethylcarbamoyl)-2-phenylcyclopropyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 213018-89-4
• 化学式: C₂₂H₃₂N₂O₅
• 分子量: 404.506
• InChiKey: JQJQLGVXXNHLSA-GSHUGGBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-tert-Butoxycarbonylamino-((1R,2S)-2-diethylcarbamoyl-2-phenyl-cyclopropyl)-acetic acid methyl ester 在 正丁基锂 、 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 tert-butyl N-[(1S)-1-[(1R,2S)-2-(diethylcarbamoyl)-2-phenylcyclopropyl]prop-2-enyl]carbamate
  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：

  二碳酸二叔丁酯 、 (1S,2R)-2-((R)-Amino-cyano-methyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide; hydrochloride 以 乙腈 为溶剂， 反应 1.5h， 以96%的产率得到(R)-tert-Butoxycarbonylamino-((1R,2S)-2-diethylcarbamoyl-2-phenyl-cyclopropyl)-acetic acid methyl ester
  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

文献信息

• Synthesis and Biological Activity of Conformationally Restricted Analogues of Milnacipran:  (1<i>S</i>,2<i>R</i>)-1-Phenyl-2-[(<i>R</i>)-1-amino-2-propynyl]<i>-N,N-</i> diethylcyclopropanecarboxamide Is a Novel Class of NMDA Receptor Channel Blocker
  作者：Satoshi Shuto、Shizuka Ono、Hiroaki Imoto、Kiyonori Yoshii、Akira Matsuda

  DOI：10.1021/jm980238m

  日期：1998.8.1

  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.