1-(4-phenylbutanoyl)-(3R,4R)-3-[1(R)-hydroxyethyl]-4-(acetoxy)-azetidin-2-one | 1197421-93-4

• 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-(4-phenylbutanoyl)-(3R,4R)-3-[1(R)-hydroxyethyl]-4-(acetoxy)-azetidin-2-one
• 英文别名: [(2R,3R)-3-[(1R)-1-hydroxyethyl]-4-oxo-1-(4-phenylbutanoyl)azetidin-2-yl] acetate
• CAS: 1197421-93-4
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: LOZABGXGQPEHQX-XQAQDONZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-联苯乙酸 、 1-(4-phenylbutanoyl)-(3R,4R)-3-[1(R)-hydroxyethyl]-4-(acetoxy)-azetidin-2-one 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77%的产率得到1-(4-phenylbutanoyl)-(3R,4R)-3-[1(R)-(biphenyl-4-ylacetyloxy)-ethyl]-4-(acetoxy)-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
• 作为产物：
  描述：

  1-(4-phenylbutanoyl)-(3R,4R)-3-[1(R)-(tert-butyldimethylsilyloxy)-ethyl]-4-(acetoxy)-azetidin-2-one 在 盐酸 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 3.5h， 以99%的产率得到1-(4-phenylbutanoyl)-(3R,4R)-3-[1(R)-hydroxyethyl]-4-(acetoxy)-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.