8-<(4-amino-1-methylbutyl)amino>-6-methoxy-4-methyl-5-<3-(trifluoromethyl)phenoxy>quinoline | 80065-55-0

• 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: 8-<(4-amino-1-methylbutyl)amino>-6-methoxy-4-methyl-5-<3-(trifluoromethyl)phenoxy>quinoline
• 英文别名: 8-(4-amino-1-methylbutylamino)-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline；5-(4-trifluoromethylphenoxy)-4-methylprimaquine；8-((4-amino-1-methylbutyl)amino)-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline；4-N-[6-methoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
• CAS: 80065-55-0
• 化学式: C₂₃H₂₆F₃N₃O₂
• 分子量: 433.474
• InChiKey: NFJRZYIWFZYFNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  69.4
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-<(4-amino-1-methylbutyl)amino>-6-methoxy-4-methyl-5-<3-(trifluoromethyl)phenoxy>quinoline 在 丁二酸 作用下， 以 乙醇 、 丙酮 、 乙腈 为溶剂， 生成 8-(4-isopropylamino-1-methylbutylamino)-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline succinate
  参考文献：
  名称：

  4-Methyl-5-(unsubstituted and substituted

  摘要：

  该类化合物包括4-甲基-5-（未取代和取代henoxy）-6-甲氧基-8-（氨基烷基氨基）喹啉作为自由碱和药学上可接受的酸胺盐。这些化合物是高效的抗疟疾药物，令人惊讶的是，它们具有组织红细胞分裂体杀灭（根治性）和血液红细胞分裂体杀灭（抑制性）活性。此外，这些药物的治疗指数显著优于普利昂奎，后者是目前组织红细胞分裂体杀灭药物的首选药物。普利昂奎在可耐受的剂量水平下没有有用的血液红细胞分裂体杀灭活性。

  公开号：

  US04431807A1
• 作为产物：
  描述：

  8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline 在 sodium tetrahydroborate 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 8-<(4-amino-1-methylbutyl)amino>-6-methoxy-4-methyl-5-<3-(trifluoromethyl)phenoxy>quinoline
  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

文献信息

• Antimalarials. 15. Side-chain analogues of 8-(4-amino-1-methylbutylamino)-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline
  作者：Maurice P. Lamontagne、Peter Blumbergs

  DOI：10.1002/jhet.5570210108

  日期：1984.1

  Six side chain analogs of the highly active antimalarial agent 8-(4-amino-1-methylbutylamino)-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline (I) were prepared and evaluated for blood and tissue schizonticidal activity. Although most examples were markedly superior to primaquine none was superior to the parent compound I.

  制备了六种高活性抗疟疾药物8-（4-氨基-1-甲基丁基氨基）-6-甲氧基-4-甲基-5-（3-三氟甲基苯氧基）喹啉（I）的侧链类似物，并对其血液和组织裂殖体进行了评估活动。尽管大多数实例均明显优于伯氨喹，但均未优于母体化合物I。
• Methods and compositions for treating diseases associated with pathogenic proteins
  申请人：Chiang K. Peter

  公开号：US20070179123A1

  公开（公告）日：2007-08-02

  Methods and compositions are provided comprising a therapeutically effective amount of a compound of formula I wherein R 1-4 , W, X, Y and Z are as defined in the specification, for inhibiting and treating diseases and disorders associated with pathogenic proteins causing neurodegenerative diseases and amyloid diseases, such as protease resistant prion proteins (PrP Sc ) and those associated with transmissible spongiform encephalopathies (TSEs), Alzheimer's Disease, amyloidosis, and the like.

  提供了一种方法和组合物，包括公式I中化合物的治疗有效量，其中R1-4，W，X，Y和Z如规范中所定义，用于抑制和治疗与致病蛋白质相关的疾病和障碍，这些致病蛋白质导致神经退行性疾病和淀粉样疾病，如蛋白酶抵抗性朊病毒蛋白（PrPSc）和与可传播性海绵状脑病（TSEs），阿尔茨海默病，淀粉样变性等相关的蛋白质。
• COMPOUNDS AFFECTING GAP JUNCTION ACTIVITY
  申请人：HUA Duy H.

  公开号：US20090143425A1

  公开（公告）日：2009-06-04

  This invention relates to novel quinoline compounds which affect gap junction activity. Also provided are methods of using such compounds and compositions containing the compounds to treat gap junction disorders.

  本发明涉及新型喹啉化合物，其影响间隙连接活性。还提供了使用这种化合物的方法和含有这种化合物的组合物来治疗间隙连接障碍。
• 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.
• LAMONTAGNE, M. P.;BLUMBERGS, P., J. HETEROCYCL. CHEM., 1984, 21, N 1, 33-35
  作者：LAMONTAGNE, M. P.、BLUMBERGS, P.

  DOI：——

  日期：——