(4-acetylphenyl)acetyl chloride | 947546-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-acetylphenyl)acetyl chloride
• 英文别名: 2-(4-Acetylphenyl)acetyl chloride
• CAS: 947546-98-7
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: SXVGEOPOJGCHIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-acetylphenyl)acetyl chloride 在 4-二甲氨基吡啶 、 sodium azide 、 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 26.0h， 生成 4-[1-(4-Acetyl-benzylcarbamoyl)-3,3-diethyl-4-oxo-azetidin-2-yloxy]-benzoic acid
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003
• 作为产物：
  描述：

  (4-乙酰基苯基)乙酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 生成 (4-acetylphenyl)acetyl chloride
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003

文献信息

• 1-(2-Arylethyl)-Pyrrolidine
  申请人：MERCK PATENT GmbH

  公开号：EP0483580A2

  公开（公告）日：1992-05-06

  Neue 1-(2-Arylethyl)-pyrrolidine der Formel I worin Ar, R¹, R² und R³ die in Patentanspruch 1 angegebene Bedeutung haben, zeigen analgetische Eigenschaften.

  式 I 的新 1-(2-芳基乙基)-吡咯烷类化合物 其中 Ar、R¹、R² 和 R³ 具有权利要求 1 所述的含义、 具有镇痛特性。
• Identification of a novel series of benzimidazoles as potent and selective antagonists of the human melanocortin-4 receptor
  作者：Lydie Poitout、Valérie Brault、Carole Sackur、Sonia Bernetière、José Camara、Pascale Plas、Pierre Roubert

  DOI：10.1016/j.bmcl.2007.06.010

  日期：2007.8

  A novel series of benzimidazoles was identified and optimized, leading to the discovery of potent and selective antagonists of the human melanocortin-4 receptor. In addition, compound 5i was shown to cross the blood-brain barrier after intravenous dosing in rats. (c) 2007 Elsevier Ltd. All rights reserved.
• US5232978A
  申请人：——

  公开号：US5232978A

  公开（公告）日：1993-08-03
• Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones
  作者：Shrenik K. Shah、Conrad P. Dorn、Paul E. Finke、Jeffrey J. Hale、William K. Hagmann、Karen A. Brause、Gilbert O. Chandler、Amy L. Kissinger、Bonnie M. Ashe

  DOI：10.1021/jm00099a003

  日期：1992.10

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.