N-(2-{6-[(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-5,8-dimethoxy-quinolin-4-yl}-phenyl)-2,2,2-trifluoro-acetamide | 362050-93-9

• 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: N-(2-{6-[(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-5,8-dimethoxy-quinolin-4-yl}-phenyl)-2,2,2-trifluoro-acetamide
• CAS: 362050-93-9
• 化学式: C₂₆H₂₂F₃N₃O₇
• 分子量: 545.472
• InChiKey: QHGBZAUALJVJOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  125.08
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-(2-{6-[(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-5,8-dimethoxy-quinolin-4-yl}-phenyl)-2,2,2-trifluoro-acetamide 在 ammonium cerium(IV) nitrate 、 硫酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以53%的产率得到N-(2-{6-[(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-5,8-dioxo-5,8-dihydro-quinolin-4-yl}-phenyl)-2,2,2-trifluoro-acetamide
  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：

  tributyl (o-tert-butyloxycarbonylaminophenyl) stannane 在 双(乙腈)氯化钯(II) 、 palladium on activated charcoal 三氟乙酸 、 环己烯 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 22.25h， 生成 N-(2-{6-[(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-5,8-dimethoxy-quinolin-4-yl}-phenyl)-2,2,2-trifluoro-acetamide
  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