4-Bromo-9-(2-nitro-phenyl)-pyrido[2,3-g]quinoline-5,10-dione | 362050-98-4

• 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-Bromo-9-(2-nitro-phenyl)-pyrido[2,3-g]quinoline-5,10-dione
• CAS: 362050-98-4
• 化学式: C₁₈H₈BrN₃O₄
• 分子量: 410.183
• InChiKey: USCPLOBRDQBAIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-Bromo-9-(2-nitro-phenyl)-pyrido[2,3-g]quinoline-5,10-dione 以 氯仿 、 水 、 三氟乙酸 为溶剂， 反应 0.08h， 以62%的产率得到4-Hydroxy-9-(2-nitro-phenyl)-pyrido[2,3-g]quinoline-5,10-dione
  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：

  o-nitrocinnamaldehyde dimethylhydrazone 、 4,6-dibromo-5,8-quinolinequinone 反应 4.0h， 以45%的产率得到4-Bromo-9-(2-nitro-phenyl)-pyrido[2,3-g]quinoline-5,10-dione
  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