6-(1-benzyl-1H-indol-3-yl)-2-hexylthieno[3,2-d]pyrimidin-4-ol | 1440957-75-4

• 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)-2-hexylthieno[3,2-d]pyrimidin-4-ol
• 英文别名: 6-(1-benzylindol-3-yl)-2-hexyl-3H-thieno[3,2-d]pyrimidin-4-one
• CAS: 1440957-75-4
• 化学式: C₂₇H₂₇N₃OS
• 分子量: 441.597
• InChiKey: SQURPIZXQBOQSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-乙酰吲哚 在 盐酸 、 4-二甲氨基吡啶 、 sodium sulfide nonahydrate 、 盐酸羟胺 、 sodium ethanolate 、 sodium acetate 、 二吡啶硫碳酸酯 、 potassium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.58h， 生成 6-(1-benzyl-1H-indol-3-yl)-2-hexylthieno[3,2-d]pyrimidin-4-ol
  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

文献信息

• 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)
  作者：Enrico Perspicace、Valérie Jouan-Hureaux、Rino Ragno、Flavio Ballante、Stefania Sartini、Concettina La Motta、Federico Da Settimo、Binbin Chen、Gilbert Kirsch、Serge Schneider、Béatrice Faivre、Stéphanie Hesse

  DOI：10.1016/j.ejmech.2013.03.022

  日期：2013.5

  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.