N-(2-bromo-4,5-dimethoxybenzyl)-5-isoquinolinamine | 736930-14-6

• 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-bromo-4,5-dimethoxybenzyl)-5-isoquinolinamine
• 英文别名: N-[(2-bromo-4,5-dimethoxyphenyl)methyl]isoquinolin-5-amine
• CAS: 736930-14-6
• 化学式: C₁₈H₁₇BrN₂O₂
• 分子量: 373.249
• InChiKey: ATZZGFIQJVSFIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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-bromo-4,5-dimethoxybenzyl)-5-isoquinolinamine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以56%的产率得到8,9-Dimethoxybenzo[c][1,8]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：

  5-氨基异喹啉 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 N-(2-bromo-4,5-dimethoxybenzyl)-5-isoquinolinamine
  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

文献信息

• Synthesis and biological evaluation of dialkylaminoalkylamino benzo[c][1,7] and [1,8]phenanthrolines as antiproliferative agents
  作者：Tuba Şerbetçi、Constance Genès、Sabine Depauw、Soizic Prado、François-Hugues Porée、Marie-Paule Hildebrand、Marie-Hélène David-Cordonnier、Sylvie Michel、François Tillequin

  DOI：10.1016/j.ejmech.2010.02.043

  日期：2010.6

  Benzo[c][1,7] and [1,8]phenanthroline substituted by dialkylaminoalkyl side chains at position C2 and C1, respectively, were synthesized and their biological activity evaluated. These compounds displayed more potent cytotoxicity toward L1210 cells than the parent unsubstituted compounds, associated with strong DNA interaction. The moderate Topol inhibitory activity induced by the novel compounds suggests that other cellular targets should be responsible for the antiproliferative activity.