3-[(chloroacetyl)amino]-5-(1H-indol-3-yl)-2-thiophenecarboxamide | 1440958-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[(chloroacetyl)amino]-5-(1H-indol-3-yl)-2-thiophenecarboxamide
• 英文别名: 3-[(2-chloroacetyl)amino]-5-(1H-indol-3-yl)thiophene-2-carboxamide
• CAS: 1440958-07-5
• 化学式: C₁₅H₁₂ClN₃O₂S
• 分子量: 333.798
• InChiKey: CGCSSENMNDUTMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(chloroacetyl)amino]-5-(1H-indol-3-yl)-2-thiophenecarboxamide 在 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.5h， 生成 6-(1H-indol-3-yl)-2-[(4-methyl-1-piperazinyl)methyl]thieno[3,2-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new classes of thieno[3,2-d]pyrimidinone and thieno[1,2,3]triazine as inhibitor of vascular endothelial growth factor receptor-2 (VEGFR-2)

  摘要：

  Driven by a multidisciplinary approach combination (Structure-Based (SB) Three-Dimensional Quantitative Structure Activity Relationships (3-D QSAR), molecular modeling, organic chemistry and various biological evaluations) here is reported the disclosure of new thienopyrimidines 1-3 as inhibitors of KDR activity and human umbilical vein endothelial cell (HUVEC) proliferation. More specifically, compound 2f represents a new lead compound that inhibits VEGFR-2 and HUVEC at mu M concentration. Moreover by the mean of an endothelial cell tube formation in vitro model 2f tartaric acid salt proved to block angiogenesis of HUVEC at mu M level. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.022
• 作为产物：
  描述：

  在 sodium ethanolate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 3-[(chloroacetyl)amino]-5-(1H-indol-3-yl)-2-thiophenecarboxamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new classes of thieno[3,2-d]pyrimidinone and thieno[1,2,3]triazine as inhibitor of vascular endothelial growth factor receptor-2 (VEGFR-2)

  摘要：

  Driven by a multidisciplinary approach combination (Structure-Based (SB) Three-Dimensional Quantitative Structure Activity Relationships (3-D QSAR), molecular modeling, organic chemistry and various biological evaluations) here is reported the disclosure of new thienopyrimidines 1-3 as inhibitors of KDR activity and human umbilical vein endothelial cell (HUVEC) proliferation. More specifically, compound 2f represents a new lead compound that inhibits VEGFR-2 and HUVEC at mu M concentration. Moreover by the mean of an endothelial cell tube formation in vitro model 2f tartaric acid salt proved to block angiogenesis of HUVEC at mu M level. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.022