6-Methoxy-5-(4-methoxyphenoxy)-4-methyl-8-nitroquinoline | 82333-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Methoxy-5-(4-methoxyphenoxy)-4-methyl-8-nitroquinoline
• 英文别名: 6-Methoxy-5-[4-methoxyphenoxy]-8-nitrolepidine
• CAS: 82333-40-2
• 化学式: C₁₈H₁₆N₂O₅
• 分子量: 340.335
• InChiKey: ZDDBRYMZIVTEKD-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C(Solv: 2-ethoxyethanol (110-80-5))
• 沸点：
  502.8±50.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-Methoxy-5-(4-methoxyphenoxy)-4-methyl-8-nitroquinoline 在 镍 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 1.25h， 以58%的产率得到8-Amino-6-methoxy-5-(4-methoxyphenoxy)-4-methylquinoline
  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
• 作为产物：
  描述：

  4-甲基-5,6-二甲氧基-8-硝基喹啉 在 盐酸 、 氢氧化钾 、 三氯氧磷 作用下， 以 乙二醇乙醚 、 乙醇 为溶剂， 反应 31.0h， 生成 6-Methoxy-5-(4-methoxyphenoxy)-4-methyl-8-nitroquinoline
  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

• 4-Methyl-5-(unsubstituted and substituted
  申请人：The United States of America as represented by the Secretary of the Army

  公开号：US04431807A1

  公开（公告）日：1984-02-14

  Compounds of the class including 4-methyl-5-(unsubstituted and substituted henoxy)-6-methoxy-8-(aminoalkylamino)quinolines as the free bases and pharmaceutically acceptable acid amine salts are described. The compounds are highly effective antimalarial agents which possess, surprisingly, both tissue schizonticidal (radical curative) and blood schizonticidal (suppressive) activity. In addition, these drugs have significantly better therapeutics indices than primaquine which is the current tissue schizonticidal drug of choice. Primaquine possesses no useful blood schizonticidal activity at tolerated dose levels.

  本类化合物包括4-甲基-5-(未取代和取代的苯氧基)-6-甲氧基-8-(氨基烷基)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，出人意料地具有组织无性红体杀灭（根治性）和血液无性红体杀灭（抑制性）活性。此外，这些药物的治疗指数显著优于目前组织无性红体杀灭药物首选的前奎宁。在可耐受的剂量水平下，前奎宁没有有用的血液无性红体杀灭活性。
• 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
• 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.