N-(2,3-dihydro-1H-inden-5-yl)-4-(pyridin-4-ylmethylthio)-1H-indole-3-carboxamide | 1149359-72-7

• 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: N-(2,3-dihydro-1H-inden-5-yl)-4-(pyridin-4-ylmethylthio)-1H-indole-3-carboxamide
• 英文别名: N-(2,3-dihydro-1H-inden-5-yl)-4-(pyridin-4-ylmethylsulfanyl)-1H-indole-3-carboxamide
• CAS: 1149359-72-7
• 化学式: C₂₄H₂₁N₃OS
• 分子量: 399.516
• InChiKey: NKUJUBCXTSRQSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚-3-甲酸甲酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三甲基铝 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 thallium(III) trifluoroacetate 作用下， 以 1,4-二氧六环 、 正己烷 、 甲苯 、 三氟乙酸 为溶剂， 反应 6.0h， 生成 N-(2,3-dihydro-1H-inden-5-yl)-4-(pyridin-4-ylmethylthio)-1H-indole-3-carboxamide
  参考文献：
  名称：

  KDR inhibitor with the intramolecular non-bonded interaction: Conformation–activity relationships of novel indole-3-carboxamide derivatives

  摘要：

  We previously reported that compound 1, having a similar conformation to PTK787 (2) by forming a pseudo ring structure with an intramolecular non-bonded S-O interaction, exhibited a potent inhibitory activity against VEGFR2 tyrosine kinase (KDR).(1) Applying the ideas of pseudo ring formations, we have designed three types of novel indole carboxamide derivatives 5-7 with an intramolecular hydrogen bonding or non-bonded S-O interaction. We describe the design and synthesis of 5-7, and also discuss the relationships of their KDR inhibitory activity and conformations that were stabilized by their intramolecular non-bonded interactions. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.063

文献信息

• KDR inhibitor with the intramolecular non-bonded interaction: Conformation–activity relationships of novel indole-3-carboxamide derivatives
  作者：Takahiro Honda、Hironori Nagahara、Hiroyuki Mogi、Masakazu Ban、Hiroyuki Aono

  DOI：10.1016/j.bmcl.2011.01.063

  日期：2011.3

  We previously reported that compound 1, having a similar conformation to PTK787 (2) by forming a pseudo ring structure with an intramolecular non-bonded S-O interaction, exhibited a potent inhibitory activity against VEGFR2 tyrosine kinase (KDR).(1) Applying the ideas of pseudo ring formations, we have designed three types of novel indole carboxamide derivatives 5-7 with an intramolecular hydrogen bonding or non-bonded S-O interaction. We describe the design and synthesis of 5-7, and also discuss the relationships of their KDR inhibitory activity and conformations that were stabilized by their intramolecular non-bonded interactions. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.