(2S)-allyl 2-((R)-1-acetoxybut-3-enyl)-5-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy)indoline-1-carboxylate | 1093077-48-5

• 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: (2S)-allyl 2-((R)-1-acetoxybut-3-enyl)-5-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy)indoline-1-carboxylate
• 英文别名: prop-2-enyl (2S)-2-[(1R)-1-acetyloxybut-3-enyl]-5-[3-(oxan-2-yloxy)propoxy]-2,3-dihydroindole-1-carboxylate
• CAS: 1093077-48-5
• 化学式: C₂₆H₃₅NO₇
• 分子量: 473.566
• InChiKey: PSNDJVMVKDYCCN-ZXABPTRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-allyl 2-((R)-1-acetoxybut-3-enyl)-5-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy)indoline-1-carboxylate 在 乙醇 、 4-甲基苯磺酸吡啶 作用下， 以88%的产率得到(S)-allyl 2-((R)-1-acetoxybut-3-enyl)-5-(3-hydroxypropoxy)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
• 作为产物：
  描述：

  (2S)-allyl 2-((R)-1-hydroxybut-3-enyl)-5-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy) indoline-1-carboxylate 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(2S)-allyl 2-((R)-1-acetoxybut-3-enyl)-5-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy)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

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.