4-butyl-12-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-bis[1,3]dioxolo[4,5-c:4',5'-j]phenanthridin-5(4H)-one | 1307740-77-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 4-butyl-12-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-bis[1,3]dioxolo[4,5-c:4',5'-j]phenanthridin-5(4H)-one
• 英文别名: 12-butyl-19-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-5,7,15,17-tetraoxa-12-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-1(20),2,4(8),9,13,18-hexaen-11-one
• CAS: 1307740-77-7
• 化学式: C₂₂H₁₇F₆NO₆
• 分子量: 505.37
• InChiKey: SMMMUHJDSPJDNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  1,3-亚甲二氧杂环戊烯-4-碘 在 copper(l) iodide 、 (氯亚甲基)二甲基氯化铵 、 palladium diacetate 、 potassium carbonate 、 caesium carbonate 、 对甲苯磺酸 、 tricyclohexylphosphine tetrafluoroborate 、 L-脯氨酸 作用下， 以 二氯甲烷 、 2,4-滴二甲胺盐 、 二甲基亚砜 、 甲苯 为溶剂， 反应 32.0h， 生成 4-butyl-12-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-bis[1,3]dioxolo[4,5-c:4',5'-j]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

文献信息

• Fused heterocyclic amido compounds as anti-hepatitis C virus agents
  作者：Hiroshi Aoyama、Kazuyuki Sugita、Masahiko Nakamura、Atsushi Aoyama、Mohammed T.A. Salim、Mika Okamoto、Masanori Baba、Yuichi Hashimoto

  DOI：10.1016/j.bmc.2011.03.002

  日期：2011.4

  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.