6-(1-benzyl-1H-indol-3-yl)-4-chlorothieno[3,2-d]pyrimidine | 1440958-05-3

• 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: 6-(1-benzyl-1H-indol-3-yl)-4-chlorothieno[3,2-d]pyrimidine
• CAS: 1440958-05-3
• 化学式: C₂₁H₁₄ClN₃S
• 分子量: 375.881
• InChiKey: VNOGAFNFIKQYKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  30.71
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-(1-benzyl-1H-indol-3-yl)-4-chlorothieno[3,2-d]pyrimidine 、 4-甲氧基苯酚 在 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到6-(1-bBenzyl-1H-indol-3-yl)-4-(4-methoxyphenoxy)thieno[3,2-d]pyrimidine
  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：

  3-amino-5-(1-benzyl-1H-indol-3-yl)-2-thiophenecarbonitrile 在 硫酸 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 6-(1-benzyl-1H-indol-3-yl)-4-chlorothieno[3,2-d]pyrimidine
  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