(9S)-2-((2-methoxyethoxy)methoxy)-6-oxo-6,9,9a,10-tetrahydropyrido[1,2-a]indol-9-yl phenylacetate | 1093077-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (9S)-2-((2-methoxyethoxy)methoxy)-6-oxo-6,9,9a,10-tetrahydropyrido[1,2-a]indol-9-yl phenylacetate
• CAS: 1093077-43-0
• 化学式: C₂₄H₂₅NO₆
• 分子量: 423.466
• InChiKey: TUMCISWDRTYIHD-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (9S)-2-((2-methoxyethoxy)methoxy)-6-oxo-6,9,9a,10-tetrahydropyrido[1,2-a]indol-9-yl phenylacetate 、 苯硫酚 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以97%的产率得到(8R,9R)-2-((2-methoxyethoxy)methoxy)-6-oxo-8-(phenylthio)-6,7,8,9,9a,10-hexahydro pyrido[1,2-a]indol-9-yl 2-phenylacetate
  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：

  苯乙酸 、 (9S)-9-hydroxy-2-((2-methoxyethoxy)methoxy)-9a,10-dihydropyrido[1,2-a]indol-6(9H)-one 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到(9S)-2-((2-methoxyethoxy)methoxy)-6-oxo-6,9,9a,10-tetrahydropyrido[1,2-a]indol-9-yl phenylacetate
  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