4-ethyl-6-methoxy-8-nitro-5-pentyloxyquinoline | 663953-18-2

• 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-pentyloxyquinoline
• 英文别名: 4-Ethyl-6-methoxy-8-nitro-5-(pentyloxy)quinoline；4-ethyl-6-methoxy-8-nitro-5-pentoxyquinoline
• CAS: 663953-18-2
• 化学式: C₁₇H₂₂N₂O₄
• 分子量: 318.373
• InChiKey: BNRFRIZSDIGXAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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-pentyloxyquinoline 在 氢气 、 镍 、 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 N8-(4-amino-1-methylpentyl)-4-ethyl-6-methoxy-5-pentyloxy-8-quinolinamine
  参考文献：
  名称：

  新型 8-喹啉胺的合成、抗疟、抗利什曼尼、抗菌、细胞毒性和高铁血红蛋白 (MetHB) 形成活性。

  摘要：

  我们报告了两个系列 8-喹啉胺的合成、体外抗原虫（针对疟原虫和利什曼原虫）、抗菌、细胞毒性（Vero 和 MetHb 产生特性）以及体内抗疟活性。N1-{4-[2-(叔丁基)-6-甲氧基-8-喹啉氨基]戊基}-(2S/2R)-2-氨基取代酰胺(21-33)和N1-[4-(4-乙基) -6-甲氧基-5-戊氧基-8-喹啉氨基)戊基]-(2S/2R)-2-氨基取代酰胺(51-63)由6-甲氧基-8-硝基喹啉和4-甲氧基-2分六步合成分别为-硝基-5-戊氧基苯胺。几种类似物在体外对恶性疟原虫 D6（氯喹敏感）和 W2（氯喹抗性）克隆表现出良好的抗疟活性，与哺乳动物细胞相比具有高选择性指数。最有前途的类似物 (21-24) 在伯氏疟原虫感染的小鼠模型中也显示出有效的体内抗疟活性。最有趣的是，许多类似物对杜氏利什曼原虫前鞭毛体表现出有前景的体外抗利什曼原虫活性，并对一组病原细菌和真菌表现出抗菌活性。与伯氨喹相比，几种类似物，尤其是

  DOI：

  10.1016/j.bmc.2006.10.036
• 作为产物：
  描述：

  1-氯-3-戊酮 、 4-methoxy-2-nitro-5-pentyloxyaniline 在 arsenic(V) oxide 、 磷酸 作用下， 生成 4-ethyl-6-methoxy-8-nitro-5-pentyloxyquinoline
  参考文献：
  名称：

  新型 8-喹啉胺的合成、抗疟、抗利什曼尼、抗菌、细胞毒性和高铁血红蛋白 (MetHB) 形成活性。

  摘要：

  我们报告了两个系列 8-喹啉胺的合成、体外抗原虫（针对疟原虫和利什曼原虫）、抗菌、细胞毒性（Vero 和 MetHb 产生特性）以及体内抗疟活性。N1-{4-[2-(叔丁基)-6-甲氧基-8-喹啉氨基]戊基}-(2S/2R)-2-氨基取代酰胺(21-33)和N1-[4-(4-乙基) -6-甲氧基-5-戊氧基-8-喹啉氨基)戊基]-(2S/2R)-2-氨基取代酰胺(51-63)由6-甲氧基-8-硝基喹啉和4-甲氧基-2分六步合成分别为-硝基-5-戊氧基苯胺。几种类似物在体外对恶性疟原虫 D6（氯喹敏感）和 W2（氯喹抗性）克隆表现出良好的抗疟活性，与哺乳动物细胞相比具有高选择性指数。最有前途的类似物 (21-24) 在伯氏疟原虫感染的小鼠模型中也显示出有效的体内抗疟活性。最有趣的是，许多类似物对杜氏利什曼原虫前鞭毛体表现出有前景的体外抗利什曼原虫活性，并对一组病原细菌和真菌表现出抗菌活性。与伯氨喹相比，几种类似物，尤其是

  DOI：

  10.1016/j.bmc.2006.10.036

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。
• 8-Quinolinamines and Their pro prodrug conjugates as potent blood-Schizontocidal antimalarial agents
  作者：Suryanarayana Vangapandu、Sandeep Sachdeva、Meenakshi Jain、Savita Singh、Prati Pal Singh、Chaman Lal Kaul、Rahul Jain

  DOI：10.1016/j.bmc.2003.07.003

  日期：2003.10

  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.
• 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
• US6979740B2
  申请人：——

  公开号：US6979740B2

  公开（公告）日：2005-12-27
• [EN] RING-SUBSTITUTED 8-AMINOQUNOLINE DERIVATES AS ANTIMALARIAL AGENTS<br/>[FR] DERIVES DE 8-AMINOQUINOLINE A CYCLE SUBSTITUE UTILES COMME AGENTS ANTI-PALUDEENS
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2004085402A1

  公开（公告）日：2004-10-07

  The present invention is concerned with the development of novel 8-aminoquinoline analogs according to formula (1) with the definitions of R, R<1>, R<2> and R<3> in the description in the treatment and prevention of malaria. The said compounds have 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. 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.