5,8-dimethoxy-6-nitro-4-(trifluoromethanesulfonyloxy)quinoline | 362050-88-2

• 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: 5,8-dimethoxy-6-nitro-4-(trifluoromethanesulfonyloxy)quinoline
• CAS: 362050-88-2
• 化学式: C₁₂H₉F₃N₂O₇S
• 分子量: 382.274
• InChiKey: DHBAHJIMIMLHMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  117.86
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5,8-dimethoxy-6-nitro-4-(trifluoromethanesulfonyloxy)quinoline 在 双(乙腈)氯化钯(II) 、 palladium on activated charcoal lithium bromide 、 环己烯 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 16.75h， 生成 6-amino-4-(2-tert-butyloxycarbonylaminophenyl)-5,8-dimethoxyquinoline
  参考文献：
  名称：

  A C-Ring Regioisomer of the Marine Alkaloid Meridine Exhibits Selective In Vitro Cytotoxicity for Solid Tumours

  摘要：

  9-Hydroxybenzo[b]pyrido[4,3,2-de](1,10)-phenantrolin-8-one (1), a regioisomer of the marine alkaloid meridine, was synthesized from 5,8-dimethoxy-6-nitro-4(1H)-quinolinone in eight steps and 23% overall yield. A shorter route was also investigated, based on the hetero Diels-Alder reaction between o-nitrocinnamaldehyde dimethylhydrazone and 4-halogen-6-bromo-5,8-quinolinequinones followed by reductive cyclization onto the C-5 carbonyl of the quinone. Compound 1 showed a remarkable in vitro cytotoxicity, with a pattern of selectivity towards solid rumours that is not found in the reference alkaloid, the activity against the human lung carcinoma (A-549) being particularly noteworthy. The activities of meridine and compound 1 as inhibitors of topoisomerase II were also significantly different. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00078-5
• 作为产物：
  描述：

  三氟甲磺酸酐 、 5,8-dimethoxy-6-nitro-4(1H)-quinolone 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以76%的产率得到5,8-dimethoxy-6-nitro-4-(trifluoromethanesulfonyloxy)quinoline
  参考文献：
  名称：

  A C-Ring Regioisomer of the Marine Alkaloid Meridine Exhibits Selective In Vitro Cytotoxicity for Solid Tumours

  摘要：

  9-Hydroxybenzo[b]pyrido[4,3,2-de](1,10)-phenantrolin-8-one (1), a regioisomer of the marine alkaloid meridine, was synthesized from 5,8-dimethoxy-6-nitro-4(1H)-quinolinone in eight steps and 23% overall yield. A shorter route was also investigated, based on the hetero Diels-Alder reaction between o-nitrocinnamaldehyde dimethylhydrazone and 4-halogen-6-bromo-5,8-quinolinequinones followed by reductive cyclization onto the C-5 carbonyl of the quinone. Compound 1 showed a remarkable in vitro cytotoxicity, with a pattern of selectivity towards solid rumours that is not found in the reference alkaloid, the activity against the human lung carcinoma (A-549) being particularly noteworthy. The activities of meridine and compound 1 as inhibitors of topoisomerase II were also significantly different. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00078-5