1-((S)-2-((S)-1-(tert-butyldimethylsilyloxy)but-3-enyl)-5-((2-methoxyethoxy)methoxy) indolin-1-yl)prop-2-en-1-one | 1093077-33-8

• 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: 1-((S)-2-((S)-1-(tert-butyldimethylsilyloxy)but-3-enyl)-5-((2-methoxyethoxy)methoxy) indolin-1-yl)prop-2-en-1-one
• 英文别名: 1-[(2S)-2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxybut-3-enyl]-5-(2-methoxyethoxymethoxy)-2,3-dihydroindol-1-yl]prop-2-en-1-one
• CAS: 1093077-33-8
• 化学式: C₂₅H₃₉NO₅Si
• 分子量: 461.674
• InChiKey: URHAWZJTWAJDSR-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-((S)-2-((S)-1-(tert-butyldimethylsilyloxy)but-3-enyl)-5-((2-methoxyethoxy)methoxy) indolin-1-yl)prop-2-en-1-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以90%的产率得到(10S,10aS,Z)-10-(tert-butyldimethylsilyloxy)-2-((2-methoxyethoxy)methoxy)-9,10,10a,11-tetrahydro-6H-azepino[1,2-a]indol-6-one
  参考文献：
  名称：

  Building skeletally diverse architectures on the Indoline Scaffold: The discovery of a chemical probe of focal adhesion kinase signaling networks

  摘要：

  Inspired by bioactive indoline alkaloid natural products, here, we report a divergent synthesis approach that led to skeletally diverse indoline alkaloid-inspired compounds. The natural product-inspired compounds obtained were then subjected to a series of in vitro and cellular assays to examine their properties as modulators of focal adhesion kinase (FAK) activity. This study resulted in the identification of a promising lead inhibitor of FAK (42), which also showed activity in a wound healing and cell invasion assay. The in silico study of the lead compound (42) was also undertaken. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.025
• 作为产物：
  描述：

  (S)-2-((S)-1-(tert-butyldimethylsilyloxy)but-3-enyl)-5-((2-methoxyethoxy)methoxy)indoline 、 丙烯酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到1-((S)-2-((S)-1-(tert-butyldimethylsilyloxy)but-3-enyl)-5-((2-methoxyethoxy)methoxy) indolin-1-yl)prop-2-en-1-one
  参考文献：
  名称：

  Building skeletally diverse architectures on the Indoline Scaffold: The discovery of a chemical probe of focal adhesion kinase signaling networks

  摘要：

  Inspired by bioactive indoline alkaloid natural products, here, we report a divergent synthesis approach that led to skeletally diverse indoline alkaloid-inspired compounds. The natural product-inspired compounds obtained were then subjected to a series of in vitro and cellular assays to examine their properties as modulators of focal adhesion kinase (FAK) activity. This study resulted in the identification of a promising lead inhibitor of FAK (42), which also showed activity in a wound healing and cell invasion assay. The in silico study of the lead compound (42) was also undertaken. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.025

文献信息

• Building skeletally diverse architectures on the Indoline Scaffold: The discovery of a chemical probe of focal adhesion kinase signaling networks
  作者：Michael Prakesch、Krikor Bijian、Valérie Campagna-Slater、Sophie Quevillon、Reni Joseph、Chang-Qing Wei、Esther Sesmilo、Ayub Reayi、Rajamohan R. Poondra、Michael L. Barnes、Donald M. Leek、Bin Xu、Caroline Lougheed、Matthieu Schapira、Moulay Alaoui-Jamali、Prabhat Arya

  DOI：10.1016/j.bmc.2008.09.025

  日期：2008.11

  Inspired by bioactive indoline alkaloid natural products, here, we report a divergent synthesis approach that led to skeletally diverse indoline alkaloid-inspired compounds. The natural product-inspired compounds obtained were then subjected to a series of in vitro and cellular assays to examine their properties as modulators of focal adhesion kinase (FAK) activity. This study resulted in the identification of a promising lead inhibitor of FAK (42), which also showed activity in a wound healing and cell invasion assay. The in silico study of the lead compound (42) was also undertaken. (C) 2008 Elsevier Ltd. All rights reserved.