4-Ethyl-6-methoxy-8-nitro-5-octoxyquinoline | 663953-21-7

• 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: 4-Ethyl-6-methoxy-8-nitro-5-octoxyquinoline
• CAS: 663953-21-7
• 化学式: C₂₀H₂₈N₂O₄
• 分子量: 360.453
• InChiKey: IUMWIXNLDXVFOV-UHFFFAOYSA-N

物化性质

• 熔点：
  40-41 °C
• 沸点：
  508.1±45.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  77.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Ethyl-6-methoxy-8-nitro-5-octoxyquinoline 在 Raney nickel (T₁ grade) 氢气 、 一水合肼 、 三乙胺 作用下， 以 乙醇 为溶剂， 120.0 ℃ 、310.26 kPa 条件下， 反应 32.75h， 生成 4-N-(4-ethyl-6-methoxy-5-octoxyquinolin-8-yl)pentane-1,4-diamine
  参考文献：
  名称：

  8-Quinolinamines and Their pro prodrug conjugates as potent blood-Schizontocidal antimalarial agents

  摘要：

  Synthesis and antimalarial activities of N-8-(4-amino-1-methylbutyl)-5-alkoxy-4-ethyl-6-methoxy-8-quinolinamines (5) and their pro prodrug analogues (6-7) prepared by covalently linking 5 to the redox-sensitive (8) and esterase-sensitive (9) linkers through the amide linkage are reported. The most effective 8-quinolinamines [5c (R = C5H11) and 5f (R = C8H17)] A have exhibited in vitro and in vivo biological efficacy superior to that of the standard drug chloroquine against both drug-sensitive and drug-resistant malaria strains. Analogues 6-7 were evaluated for in vivo blood-schizontocidal activity as potential pro prodrug models for the primary amino group containing 8-quinolinamines (5). The most effective pro prodrug analogue (6c) has displayed promising activities against drug-sensitive and drug-resistant strains of Plasmodia in vivo. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.07.003
• 作为产物：
  描述：

  1-氯-3-戊酮 、 4-methoxy-2-nitro-5-octoxyaniline 在 arsenic(V) oxide 、 磷酸 作用下， 反应 3.0h， 以32%的产率得到4-Ethyl-6-methoxy-8-nitro-5-octoxyquinoline
  参考文献：
  名称：

  8-Quinolinamines and Their pro prodrug conjugates as potent blood-Schizontocidal antimalarial agents

  摘要：

  Synthesis and antimalarial activities of N-8-(4-amino-1-methylbutyl)-5-alkoxy-4-ethyl-6-methoxy-8-quinolinamines (5) and their pro prodrug analogues (6-7) prepared by covalently linking 5 to the redox-sensitive (8) and esterase-sensitive (9) linkers through the amide linkage are reported. The most effective 8-quinolinamines [5c (R = C5H11) and 5f (R = C8H17)] A have exhibited in vitro and in vivo biological efficacy superior to that of the standard drug chloroquine against both drug-sensitive and drug-resistant malaria strains. Analogues 6-7 were evaluated for in vivo blood-schizontocidal activity as potential pro prodrug models for the primary amino group containing 8-quinolinamines (5). The most effective pro prodrug analogue (6c) has displayed promising activities against drug-sensitive and drug-resistant strains of Plasmodia in vivo. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.07.003

文献信息

• Process for preparation of ring-substituted 8-aminoquinoline analogs as antimalarial agents
  申请人：——

  公开号：US20040192724A1

  公开（公告）日：2004-09-30

  The present invention is concerned with the development of novel 8-aminoquinoline analogs in the treatment and prevention of malaria and the said compound has broad spectrum of activity against the blood as well as tissue stages of the human malaria parasites makes these compounds very attractive in the cure and prevention of malaria caused by drug-sensitive and multidrug resistant strains and also it is expected that development of these compounds as ideal antimalarial agents may lead to suppression as well as radical cure of the malaria infection with single drug therapy.

  本发明涉及新型8-氨基喹啉类似物在治疗和预防疟疾方面的开发，所述化合物对人类疟原虫的血期及组织期具有广谱活性，使得这些化合物在治疗和预防由药物敏感和多药耐药菌株引起的疟疾方面极具吸引力。同时，预期将这些化合物开发为理想的抗疟药物可能会导致单一药物疗法既能抑制又能根治疟疾感染。
• RING-SUBSTITUTED 8-AMINOQUINOLINE DERIVATIVES AS ANTIMALARIAL AGENTS
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：EP1606263A1

  公开（公告）日：2005-12-21
• JP2006521284A
  申请人：——

  公开号：JP2006521284A

  公开（公告）日：2006-09-21
• 抗マラリア薬としての環置換８−アミノキノリン誘導体
  申请人：カウンシル・オブ・サイエンティフィック・アンド・インダストリアル・リサーチ

  公开号：JP4727233B2

  公开（公告）日：2006-09-21
• US6979740B2
  申请人：——

  公开号：US6979740B2

  公开（公告）日：2005-12-27