(S)-allyl 2-((S)-1-(tert-butyldimethylsilyloxy)but-3-enyl)-5-((2-methoxyethoxy)methoxy) indoline-1-carboxylate | 957625-93-3

• 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: (S)-allyl 2-((S)-1-(tert-butyldimethylsilyloxy)but-3-enyl)-5-((2-methoxyethoxy)methoxy) indoline-1-carboxylate
• 英文别名: prop-2-enyl (2S)-2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxybut-3-enyl]-5-(2-methoxyethoxymethoxy)-2,3-dihydroindole-1-carboxylate
• CAS: 957625-93-3
• 化学式: C₂₆H₄₁NO₆Si
• 分子量: 491.7
• InChiKey: LLDCLJWYZBGHHG-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-allyl 2-((S)-1-(tert-butyldimethylsilyloxy)but-3-enyl)-5-((2-methoxyethoxy)methoxy) indoline-1-carboxylate 在 吗啉 、 四(三苯基膦)钯 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到(S)-2-((S)-1-(tert-butyldimethylsilyloxy)but-3-enyl)-5-((2-methoxyethoxy)methoxy)indoline
  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)-allyl 2-((S)-1-hydroxybut-3-enyl)-5-((2-methoxyethoxy)methoxy)indoline-1-carboxylate 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以83%的产率得到(S)-allyl 2-((S)-1-(tert-butyldimethylsilyloxy)but-3-enyl)-5-((2-methoxyethoxy)methoxy) indoline-1-carboxylate
  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