5-(2,4-Dichlorophenoxy)-6-methoxy-4-methyl-8-((4-phthalimido-1-methylbutyl)amino)quinoline | 82333-47-9

• 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: 5-(2,4-Dichlorophenoxy)-6-methoxy-4-methyl-8-((4-phthalimido-1-methylbutyl)amino)quinoline
• 英文别名: 2-[4-[[5-(2,4-Dichlorophenoxy)-6-methoxy-4-methylquinolin-8-yl]amino]pentyl]isoindole-1,3-dione
• CAS: 82333-47-9
• 化学式: C₃₀H₂₇Cl₂N₃O₄
• 分子量: 564.468
• InChiKey: AEMQBUHDQVMHSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2,4-Dichlorophenoxy)-6-methoxy-4-methyl-8-((4-phthalimido-1-methylbutyl)amino)quinoline 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 N4-(5-(2,4-dichlorophenoxy)-6-methoxy-4-methylquinolin-8-yl)pentane-1,4-diamine succinate
  参考文献：
  名称：

  Inhibition of human monoamine oxidase A and B by 5-phenoxy 8-aminoquinoline analogs

  摘要：

  8-Aminoquinolines (8-AQs) are important class of anti-infective therapeutics. 5-Phenoxy 8-aminoquinoline analogs have shown improved metabolic stability compared to primaquine. In view or predictive role of monoamine oxidases (MAO) in metabolism of 8-aminoquinolines the 5-phenoxy analogs were evaluated in vitro for the inhibition of recombinant human MAO-A and MAO-B. The analogs were several folds more potent inhibitors of MAO-A and MAO-B compared to primaquine, the parent drug, with selectivity for MAO-B. 5-(4-Trifluoromethylphenoxy)-4-methylprimaquine (6) Inhibited MAO-B with IC50 value of 150 nM (626-fold more potent than primaquine). These results will have important implications in optimizing metabolic stability of 8-AQs to improve therapeutic value and also indicate scope for development of 8-AQs as selective MAO inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.108
• 作为产物：
  描述：

  5-chloro-6-methoxy-4-methyl-8-nitroquinoline 在 镍 氢氧化钾 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙二醇乙醚 、 乙醇 为溶剂， 105.0 ℃ 、310.27 kPa 条件下， 反应 15.75h， 生成 5-(2,4-Dichlorophenoxy)-6-methoxy-4-methyl-8-((4-phthalimido-1-methylbutyl)amino)quinoline
  参考文献：
  名称：

  Antimalarials. 14. 5-(Aryloxy)-4-methylprimaquine analogs. A highly effective series of blood and tissue schizonticidal agents

  摘要：

  A series of five 5-(aryloxy)-4-methylprimaquine analogues has been prepared and evaluated for antimalarial activity. The compounds were tested for suppressive activity against Plasmodium berghei in mice and for radical curative activity against Plasmodium cynomolgi in the rhesus monkey. The compounds were not only significantly superior to primaquine as radical curative agents but also were suprisingly highly effective as suppressive agents.

  DOI：

  10.1021/jm00351a017

文献信息

• LAMONTAGNE, M. P.;BLUMBERGS, P.;STRUBE, R. E., J. MED. CHEM., 1982, 25, N 9, 1094-1097
  作者：LAMONTAGNE, M. P.、BLUMBERGS, P.、STRUBE, R. E.

  DOI：——

  日期：——
• US4431807A
  申请人：——

  公开号：US4431807A

  公开（公告）日：1984-02-14
• Inhibition of human monoamine oxidase A and B by 5-phenoxy 8-aminoquinoline analogs
  作者：Narayan D. Chaurasiya、Shobana Ganesan、N.P. Dhammika Nanayakkara、Luiza R.S. Dias、Larry A. Walker、Babu L. Tekwani

  DOI：10.1016/j.bmcl.2011.12.108

  日期：2012.2

  8-Aminoquinolines (8-AQs) are important class of anti-infective therapeutics. 5-Phenoxy 8-aminoquinoline analogs have shown improved metabolic stability compared to primaquine. In view or predictive role of monoamine oxidases (MAO) in metabolism of 8-aminoquinolines the 5-phenoxy analogs were evaluated in vitro for the inhibition of recombinant human MAO-A and MAO-B. The analogs were several folds more potent inhibitors of MAO-A and MAO-B compared to primaquine, the parent drug, with selectivity for MAO-B. 5-(4-Trifluoromethylphenoxy)-4-methylprimaquine (6) Inhibited MAO-B with IC50 value of 150 nM (626-fold more potent than primaquine). These results will have important implications in optimizing metabolic stability of 8-AQs to improve therapeutic value and also indicate scope for development of 8-AQs as selective MAO inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.
• Antimalarials. 14. 5-(Aryloxy)-4-methylprimaquine analogs. A highly effective series of blood and tissue schizonticidal agents
  作者：Maurice P. LaMontagne、Peter Blumbergs、Richard E. Strube

  DOI：10.1021/jm00351a017

  日期：1982.9

  A series of five 5-(aryloxy)-4-methylprimaquine analogues has been prepared and evaluated for antimalarial activity. The compounds were tested for suppressive activity against Plasmodium berghei in mice and for radical curative activity against Plasmodium cynomolgi in the rhesus monkey. The compounds were not only significantly superior to primaquine as radical curative agents but also were suprisingly highly effective as suppressive agents.