4-(2-tert-butyloxycarbonylaminophenyl)-6-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidenemethylamino)-5,8-dimethoxyquinoline | 362050-92-8

• 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: 4-(2-tert-butyloxycarbonylaminophenyl)-6-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidenemethylamino)-5,8-dimethoxyquinoline
• CAS: 362050-92-8
• 化学式: C₂₉H₃₁N₃O₈
• 分子量: 549.58
• InChiKey: FUPNRLWSBYIDLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  40.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  134.31
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸酐 、 4-(2-tert-butyloxycarbonylaminophenyl)-6-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidenemethylamino)-5,8-dimethoxyquinoline 在 三氟乙酸 作用下， 反应 1.5h， 以100%的产率得到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
• 作为产物：
  描述：

  tributyl (o-tert-butyloxycarbonylaminophenyl) stannane 在 双(乙腈)氯化钯(II) 、 palladium on activated charcoal 环己烯 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 20.75h， 生成 4-(2-tert-butyloxycarbonylaminophenyl)-6-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidenemethylamino)-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