4-(2-carbethoxybenzamido)acetylphenol | 121867-25-2

• 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: 4-(2-carbethoxybenzamido)acetylphenol
• 英文别名: Ethyl 2-[(4-acetyloxybenzoyl)amino]benzoate
• CAS: 121867-25-2
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: KJEANMZQBBFUGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-carbethoxybenzamido)acetylphenol 在 盐酸 作用下， 以 乙醇 为溶剂， 以30%的产率得到4-(carbethoxybenzamido)phenol
  参考文献：
  名称：

  Ester derivatives of 2,6-bis(1-pyrrolidinylmethyl)-4-benzamidophenol as short-acting antiarrhythmic agents. 1

  摘要：

  In an effort to find a replacement for the iv antiarrhythmic drug lidocaine having reduced systemic and central nervous system effects, activity against supraventricular as well as ventricular arrhythmias, and a biological half-life of less than 15 min, derivatives of the orally active class Ic clinical agent 2,6-bis(1-pyrrolidinylmethyl)-4-benzamidophenol, 1 (ACC-9358), were synthesized and tested. Compounds with ester groups attached to the phenyl ring were either weakly active or toxic. Replacement of the formanilide function with alkyl esters afforded compounds with antiarrhythmic activity in the range of 1. When the ester carboxyl was separated from the bis(aminomethyl)phenol by methylene units, very short half-lives were observed in human blood. In general, these compounds also had low lipophilic character.

  DOI：

  10.1021/jm00128a037
• 作为产物：
  描述：

  4-acetoxybenzoyl chloride 、 2-氨基苯甲酸乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以38%的产率得到4-(2-carbethoxybenzamido)acetylphenol
  参考文献：
  名称：

  Ester derivatives of 2,6-bis(1-pyrrolidinylmethyl)-4-benzamidophenol as short-acting antiarrhythmic agents. 1

  摘要：

  In an effort to find a replacement for the iv antiarrhythmic drug lidocaine having reduced systemic and central nervous system effects, activity against supraventricular as well as ventricular arrhythmias, and a biological half-life of less than 15 min, derivatives of the orally active class Ic clinical agent 2,6-bis(1-pyrrolidinylmethyl)-4-benzamidophenol, 1 (ACC-9358), were synthesized and tested. Compounds with ester groups attached to the phenyl ring were either weakly active or toxic. Replacement of the formanilide function with alkyl esters afforded compounds with antiarrhythmic activity in the range of 1. When the ester carboxyl was separated from the bis(aminomethyl)phenol by methylene units, very short half-lives were observed in human blood. In general, these compounds also had low lipophilic character.

  DOI：

  10.1021/jm00128a037

文献信息

• STOUT, DAVID M.;BLACK, LAWRENCE A.;BARCELON-YANG, CYNTHIA;MATIER, W. L.;B+, J. MED. CHEM., 32,(1989) N, C. 1910-1913
  作者：STOUT, DAVID M.、BLACK, LAWRENCE A.、BARCELON-YANG, CYNTHIA、MATIER, W. L.、B+

  DOI：——

  日期：——
• Ester derivatives of 2,6-bis(1-pyrrolidinylmethyl)-4-benzamidophenol as short-acting antiarrhythmic agents. 1
  作者：David M. Stout、Lawrence A. Black、Cynthia Barcelon-Yang、W. L. Matier、Barry S. Brown、Check Y. Quon、Herman F. Stampfli

  DOI：10.1021/jm00128a037

  日期：1989.8

  In an effort to find a replacement for the iv antiarrhythmic drug lidocaine having reduced systemic and central nervous system effects, activity against supraventricular as well as ventricular arrhythmias, and a biological half-life of less than 15 min, derivatives of the orally active class Ic clinical agent 2,6-bis(1-pyrrolidinylmethyl)-4-benzamidophenol, 1 (ACC-9358), were synthesized and tested. Compounds with ester groups attached to the phenyl ring were either weakly active or toxic. Replacement of the formanilide function with alkyl esters afforded compounds with antiarrhythmic activity in the range of 1. When the ester carboxyl was separated from the bis(aminomethyl)phenol by methylene units, very short half-lives were observed in human blood. In general, these compounds also had low lipophilic character.