11-(2-benzyloxy-1,1,1,3,3,3-hexafluoropropan-2-yl)-4-butyl-7,10-dimethoxy-[1,3]dioxolo[4,5-c]phenanthridin-5(4H)-one | 1307741-87-2

• 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: 11-(2-benzyloxy-1,1,1,3,3,3-hexafluoropropan-2-yl)-4-butyl-7,10-dimethoxy-[1,3]dioxolo[4,5-c]phenanthridin-5(4H)-one
• CAS: 1307741-87-2
• 化学式: C₃₀H₂₇F₆NO₆
• 分子量: 611.538
• InChiKey: ZZKADESFHTYPKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.24
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  68.15
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  11-(2-benzyloxy-1,1,1,3,3,3-hexafluoropropan-2-yl)-4-butyl-7,10-dimethoxy-[1,3]dioxolo[4,5-c]phenanthridin-5(4H)-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以82%的产率得到4-butyl-11-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-7,10-dimethoxy-[1,3]dioxolo[4,5-c]phenanthridin-5(4H)-one
  参考文献：
  名称：

  Fused heterocyclic amido compounds as anti-hepatitis C virus agents

  摘要：

  We identified a fused heteroaromatic amido structure based on the phenanthridine skeleton as a superior scaffold for candidate drugs with potent anti-HCV activity. Among the compounds synthesized, a phenanthridine analogue with a 1,3-dioxolyl group (24) possessed the most potent anti-HCV activity (EC50 value: 50 nM), with acceptable cytotoxicity. The structural development and structure-activity relationships of these compounds are described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.002
• 作为产物：
  描述：

  2-(7-(butylamino)-5-methoxybenzo[d][1,3]dioxol-4-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol 在 (氯亚甲基)二甲基氯化铵 、 palladium diacetate 、 potassium carbonate 、 caesium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 二氯甲烷 、 2,4-滴二甲胺盐 、 丙酮 为溶剂， 反应 7.0h， 生成 11-(2-benzyloxy-1,1,1,3,3,3-hexafluoropropan-2-yl)-4-butyl-7,10-dimethoxy-[1,3]dioxolo[4,5-c]phenanthridin-5(4H)-one
  参考文献：
  名称：

  Fused heterocyclic amido compounds as anti-hepatitis C virus agents

  摘要：

  We identified a fused heteroaromatic amido structure based on the phenanthridine skeleton as a superior scaffold for candidate drugs with potent anti-HCV activity. Among the compounds synthesized, a phenanthridine analogue with a 1,3-dioxolyl group (24) possessed the most potent anti-HCV activity (EC50 value: 50 nM), with acceptable cytotoxicity. The structural development and structure-activity relationships of these compounds are described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.002