1-(3-phenylpropanoyl)-(3S)-3-[1(R)-(5-phenylpentanoyloxy)-ethyl]-azetidin-2-one | 1197422-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-(3-phenylpropanoyl)-(3S)-3-[1(R)-(5-phenylpentanoyloxy)-ethyl]-azetidin-2-one
• 英文别名: [(1R)-1-[(3S)-2-oxo-1-(3-phenylpropanoyl)azetidin-3-yl]ethyl] 5-phenylpentanoate
• CAS: 1197422-07-3
• 化学式: C₂₅H₂₉NO₄
• 分子量: 407.51
• InChiKey: LHPSWJWBZZXTIV-KNQAVFIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(3-phenylpropanoyl)-(3S)-3-[1(R)-hydroxyethyl]-azetidin-2-one 、 5-苯基戊酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以59%的产率得到1-(3-phenylpropanoyl)-(3S)-3-[1(R)-(5-phenylpentanoyloxy)-ethyl]-azetidin-2-one
  参考文献：
  名称：

  β-Lactams Derived from a Carbapenem Chiron Are Selective Inhibitors of Human Fatty Acid Amide Hydrolase versus Human Monoacylglycerol Lipase

  摘要：

  A library of 30 beta-lactams has been prepared from (3R,4R)-3-[(R)-1'-(tbutyldimethylsilyloxy)-ethyl]-4-acetoxy-2-azetidinone, and the corresponding deacetoxy derivative, by sequential N- and O-functionalizations with various omega-alkenoyl and omega-arylalkanoyl chains. All compounds were selective inhibitors of hFAAH versus hMGL, and IC50 values in the nanomolar range (5-14 nM) were recorded for the best representatives. From time-dependent preincubation and rapid dilution studies, and from docking analyses in a homology model of the target enzyme, a reversible mechanism of inhibition of hFAAH is proposed.

  DOI：

  10.1021/jm9008532

文献信息

• β-Lactams Derived from a Carbapenem Chiron Are Selective Inhibitors of Human Fatty Acid Amide Hydrolase versus Human Monoacylglycerol Lipase
  作者：Marion Feledziak、Catherine Michaux、Allan Urbach、Geoffray Labar、Giulio G. Muccioli、Didier M. Lambert、Jacqueline Marchand-Brynaert

  DOI：10.1021/jm9008532

  日期：2009.11.26

  A library of 30 beta-lactams has been prepared from (3R,4R)-3-[(R)-1'-(tbutyldimethylsilyloxy)-ethyl]-4-acetoxy-2-azetidinone, and the corresponding deacetoxy derivative, by sequential N- and O-functionalizations with various omega-alkenoyl and omega-arylalkanoyl chains. All compounds were selective inhibitors of hFAAH versus hMGL, and IC50 values in the nanomolar range (5-14 nM) were recorded for the best representatives. From time-dependent preincubation and rapid dilution studies, and from docking analyses in a homology model of the target enzyme, a reversible mechanism of inhibition of hFAAH is proposed.