N-(2-chloro-4,5-methylenedioxybenzyl)-5-quinolinamine | 736930-13-5

• 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-chloro-4,5-methylenedioxybenzyl)-5-quinolinamine
• 英文别名: N-[(6-chloro-1,3-benzodioxol-5-yl)methyl]quinolin-5-amine
• CAS: 736930-13-5
• 化学式: C₁₇H₁₃ClN₂O₂
• 分子量: 312.755
• InChiKey: YVPXVOQVWUHXDD-UHFFFAOYSA-N

物化性质

• 熔点：
  259 °C(Solv: toluene (108-88-3))
• 沸点：
  493.2±45.0 °C(Predicted)
• 密度：
  1.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.38
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(2-chloro-4,5-methylenedioxybenzyl)-5-quinolinamine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 [1,3]Benzodioxolo[5,6-c][1,7]phenanthroline
  参考文献：
  名称：

  Synthesis and cytotoxic activity of benzo[c][1,7] and [1,8]phenanthrolines analogues of nitidine and fagaronine

  摘要：

  Fagaronine and nitidine are natural benzo[c] phenanthridinium alkaloids, which display antileukemic activity. Both act as topoisomerase I and topoisomerase 11 inhibitors. The objective of the present study was to prepare noncharged isosters of these compounds, with replacement of the aromatic A ring by a pyridine ring, present in other topoisomerase I inhibitors. Various 7,8- and 8,9-dimethoxy and metylenedioxy benzo[c][1,7] and [1,8]phenanthrolines were readily synthesized by benzyne-mediated cyclization of the corresponding substituted N-(2-halobenzyl)-5-quinolinamines or 5-isoquinolinamines. In both series, compounds bearing oxygenated substituents at positions 8 and 9 exhibited cytotoxic properties towards L1210 murine leukemia cells, which may result from their capacities to intercalate into DNA. Topoisomerase I inhibition was observed for all active compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.038
• 作为产物：
  描述：

  N-(quinolin-5-yl)-2-chloro-4,5-methylenedioxyphenylmethanimide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以97%的产率得到N-(2-chloro-4,5-methylenedioxybenzyl)-5-quinolinamine
  参考文献：
  名称：

  Synthesis and cytotoxic activity of benzo[c][1,7] and [1,8]phenanthrolines analogues of nitidine and fagaronine

  摘要：

  Fagaronine and nitidine are natural benzo[c] phenanthridinium alkaloids, which display antileukemic activity. Both act as topoisomerase I and topoisomerase 11 inhibitors. The objective of the present study was to prepare noncharged isosters of these compounds, with replacement of the aromatic A ring by a pyridine ring, present in other topoisomerase I inhibitors. Various 7,8- and 8,9-dimethoxy and metylenedioxy benzo[c][1,7] and [1,8]phenanthrolines were readily synthesized by benzyne-mediated cyclization of the corresponding substituted N-(2-halobenzyl)-5-quinolinamines or 5-isoquinolinamines. In both series, compounds bearing oxygenated substituents at positions 8 and 9 exhibited cytotoxic properties towards L1210 murine leukemia cells, which may result from their capacities to intercalate into DNA. Topoisomerase I inhibition was observed for all active compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.038