5-butyl-2-(1',1',1',3',3',3'-hexafluoro-2'-hydroxypropan-2'-yl)-[1,3] dioxolo[4,5-j] phenanthridin-6(5H)-one | 1307740-74-4

• 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: 5-butyl-2-(1',1',1',3',3',3'-hexafluoro-2'-hydroxypropan-2'-yl)-[1,3] dioxolo[4,5-j] phenanthridin-6(5H)-one
• 英文别名: 5-Butyl-2-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-[1,3]dioxolo[4,5-j]phenanthridin-6-one；5-butyl-2-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-[1,3]dioxolo[4,5-j]phenanthridin-6-one
• CAS: 1307740-74-4
• 化学式: C₂₁H₁₇F₆NO₄
• 分子量: 461.361
• InChiKey: ABBDVHWEHHPSLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  6-bromo-N-butyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]benzo[d][1,3]dioxole-5-carboxamide 在 palladium diacetate 、 caesium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 2,4-滴二甲胺盐 为溶剂， 反应 3.0h， 以78%的产率得到5-butyl-2-(1',1',1',3',3',3'-hexafluoro-2'-hydroxypropan-2'-yl)-[1,3] dioxolo[4,5-j] phenanthridin-6(5H)-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

• THERAPEUTIC AGENT FOR HEPATITIS C
  申请人：Baba Masanori

  公开号：US20120316342A1

  公开（公告）日：2012-12-13

  This invention provides a therapeutic agent for hepatitis C comprising, as an active ingredient, a compound having anti-HCV activity useful in treatment of hepatitis C. The therapeutic agent for hepatitis C comprises, as an active ingredient, a compound represented by formula (I) or a pharmaceutically acceptable salt thereof.

  这项发明提供了一种治疗丙型肝炎的药剂，其活性成分为具有抗丙型肝炎病毒活性的化合物，可用于治疗丙型肝炎。治疗丙型肝炎的药剂的活性成分包括由式（I）表示的化合物或其药用可接受的盐。
• 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.