10-bromo-3-(iodomethyl)-7-methoxy-3,4-dihydro-1H-[1,4]oxazino[4,3-a]indol-1-one | 1620658-51-6

• 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: 10-bromo-3-(iodomethyl)-7-methoxy-3,4-dihydro-1H-[1,4]oxazino[4,3-a]indol-1-one
• CAS: 1620658-51-6
• 化学式: C₁₃H₁₁BrINO₃
• 分子量: 436.044
• InChiKey: NWDRKCLTYFMUQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  10-bromo-3-(iodomethyl)-7-methoxy-3,4-dihydro-1H-[1,4]oxazino[4,3-a]indol-1-one 在 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 以76%的产率得到11-bromo-4-hydroxy-8-methoxy-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of tetrahydro[1,4]diazepino[1,2-a]indol-1-ones as cyclin-dependent kinase inhibitors

  摘要：

  New series of 2,3,4,5-tetrahydro[1,4]diazepino[1,2-a]indol-1-ones and 3,4,5,10-tetrahydro-2H-diazepino[3,4-b]indol-1-ones have been synthesized through an iodolactonisation/lactone-to-lactam rearrangement sequence. These compounds were evaluated as potential protein kinase inhibitors (CDK1, CDK5 and GSK-3). 11-Iodo-2,3,4,5-tetrahydro[1,4]diazepino[1,2-a]indol-1-one derivatives exhibited sub-micromolar inhibitory activity against cyclin-dependent kinases. Docking studies were realized to determine the binding mode of the inhibitors into the ATP binding domain of the CDK5 catalytic site. Our result highlighted two weak Van-der-Waals bonding interactions established between the iodine atom and both phenyl group of Phe 80 and ammonium end of Lys 33.

  DOI：

  10.1016/j.ejmech.2014.06.063
• 作为产物：
  描述：

  1-allyl-3-bromo-6-methoxy-1H-indole-2-carboxylic acid 在 2,6-二甲基吡啶 、 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以33%的产率得到10-bromo-3-(iodomethyl)-7-methoxy-3,4-dihydro-1H-[1,4]oxazino[4,3-a]indol-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of tetrahydro[1,4]diazepino[1,2-a]indol-1-ones as cyclin-dependent kinase inhibitors

  摘要：

  New series of 2,3,4,5-tetrahydro[1,4]diazepino[1,2-a]indol-1-ones and 3,4,5,10-tetrahydro-2H-diazepino[3,4-b]indol-1-ones have been synthesized through an iodolactonisation/lactone-to-lactam rearrangement sequence. These compounds were evaluated as potential protein kinase inhibitors (CDK1, CDK5 and GSK-3). 11-Iodo-2,3,4,5-tetrahydro[1,4]diazepino[1,2-a]indol-1-one derivatives exhibited sub-micromolar inhibitory activity against cyclin-dependent kinases. Docking studies were realized to determine the binding mode of the inhibitors into the ATP binding domain of the CDK5 catalytic site. Our result highlighted two weak Van-der-Waals bonding interactions established between the iodine atom and both phenyl group of Phe 80 and ammonium end of Lys 33.

  DOI：

  10.1016/j.ejmech.2014.06.063