3-(3-bromo-propionylamino)-4-chloro-benzofuran-2-carboxylic acid methyl ester | 1139838-95-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-(3-bromo-propionylamino)-4-chloro-benzofuran-2-carboxylic acid methyl ester
• 英文别名: Methyl 3-(3-bromopropanoylamino)-4-chloro-1-benzofuran-2-carboxylate
• CAS: 1139838-95-1
• 化学式: C₁₃H₁₁BrClNO₄
• 分子量: 360.592
• InChiKey: GROZSFUPSDLAOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-bromo-propionylamino)-4-chloro-benzofuran-2-carboxylic acid methyl ester 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到3-acryloylamino-4-chloro-benzofuran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of 3-substituted-benzofuran-2-carboxylic esters as a novel class of ischemic cell death inhibitors

  摘要：

  A series of 3-substituted-benzofuran-2-carboxylic esters was synthesized and evaluated for biological activity as ischemic cell death inhibitors in H9c2 cells and rat primary cardiac myocytes under conditions of oxygen and glucose deprivation. The introduction of a sulfur atom at the three-position substituent of the benzofuran ring markedly improved ischemic cell death inhibitory potency. In particular, 3-[2-(4-nitro-phenylsulfanyl)-acetylamino]-benzofuran-2-carboxylic acid ester (10) (EC(50) = 0.532 mu M, cell death = 6.18%) and 4-chloro-3-[3-(pyridin-2-ylsulfanyl)-propionylamino]-benzofuran-2-carboxylic ester (18) (EC(50) = 0.557 mu M, cell death = 7.02%) were shown to be the most potent in this series of benzofuran analogs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.102
• 作为产物：
  描述：

  3-amino-4-chloro-benzofuran-2-carboxylic acid methyl ester 、 3-溴丙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到3-(3-bromo-propionylamino)-4-chloro-benzofuran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of 3-substituted-benzofuran-2-carboxylic esters as a novel class of ischemic cell death inhibitors

  摘要：

  A series of 3-substituted-benzofuran-2-carboxylic esters was synthesized and evaluated for biological activity as ischemic cell death inhibitors in H9c2 cells and rat primary cardiac myocytes under conditions of oxygen and glucose deprivation. The introduction of a sulfur atom at the three-position substituent of the benzofuran ring markedly improved ischemic cell death inhibitory potency. In particular, 3-[2-(4-nitro-phenylsulfanyl)-acetylamino]-benzofuran-2-carboxylic acid ester (10) (EC(50) = 0.532 mu M, cell death = 6.18%) and 4-chloro-3-[3-(pyridin-2-ylsulfanyl)-propionylamino]-benzofuran-2-carboxylic ester (18) (EC(50) = 0.557 mu M, cell death = 7.02%) were shown to be the most potent in this series of benzofuran analogs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.102

文献信息

• [EN] BENZOFURAN AND BENZOTHIOPHENE DERIVATIVES SUBSTITUTED WITH AMIDE, PROCESS FOR THE PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME<br/>[FR] DÉRIVÉS DE BENZOFURANE ET DE BENZOTHIOPHÈNE À SUBSTITUTION AMIDE, PROCÉDÉ DE PRÉPARATION DE CEUX-CI ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CEUX-CI
  申请人：KOREA RES INST CHEM TECH

  公开号：WO2009048274A3

  公开（公告）日：2010-07-01
• Synthesis and biological evaluation of 3-substituted-benzofuran-2-carboxylic esters as a novel class of ischemic cell death inhibitors
  作者：Jeehee Suh、Kyu Yang Yi、Yun-Suk Lee、Eunhee Kim、Eul Kgun Yum、Sung-eun Yoo

  DOI：10.1016/j.bmcl.2010.09.102

  日期：2010.11

  A series of 3-substituted-benzofuran-2-carboxylic esters was synthesized and evaluated for biological activity as ischemic cell death inhibitors in H9c2 cells and rat primary cardiac myocytes under conditions of oxygen and glucose deprivation. The introduction of a sulfur atom at the three-position substituent of the benzofuran ring markedly improved ischemic cell death inhibitory potency. In particular, 3-[2-(4-nitro-phenylsulfanyl)-acetylamino]-benzofuran-2-carboxylic acid ester (10) (EC(50) = 0.532 mu M, cell death = 6.18%) and 4-chloro-3-[3-(pyridin-2-ylsulfanyl)-propionylamino]-benzofuran-2-carboxylic ester (18) (EC(50) = 0.557 mu M, cell death = 7.02%) were shown to be the most potent in this series of benzofuran analogs. (C) 2010 Elsevier Ltd. All rights reserved.