5,6-二甲氧基-8-硝基喹啉 | 5333-02-8

• 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
• 中文名称: 5,6-二甲氧基-8-硝基喹啉
• 英文名称: 5,6-dimethoxy-8-nitroquinoline
• CAS: 5333-02-8
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: HDOJSHDBNBHDIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  77.2
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  5,6-二甲氧基-8-硝基喹啉 在 叔丁基过氧化氢 、 碘 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以82%的产率得到3-iodo-5,6-dimethoxy-8-nitroquinoline
  参考文献：
  名称：

  Metal-free synthesis of N-fused heterocyclic iodides via C–H functionalization mediated by tert-butylhydroperoxide

  摘要：

  直接、区域选择性和无金属合成杂环碘化物的报道。

  DOI：

  10.1039/c5cc04013b
• 作为产物：
  描述：

  6-甲氧基-8-硝基喹啉 在 吡啶 、 氯仿 、 溴 、 铁粉 、 calcium carbonate 作用下， 生成 5,6-二甲氧基-8-硝基喹啉
  参考文献：
  名称：

  Further Syntheses of Primaquine Analogs¹

  摘要：

  DOI：

  10.1021/ja01623a039

文献信息

• Process for production of 8-NHR quinolines
  申请人：The United States of America as represented by the Secretary of the Army

  公开号：US04167638A1

  公开（公告）日：1979-09-11

  An improved process for producing 8-NHR quinolines from 8-aminoquinolines disclosed. The process comprises reacting 8-aminoquinolines with a substituted alkyl halide in the presence of an amine having a boiling point of 80.degree.-90.degree. C. The amine functions as an acid acceptor whereby the amine salt formed may be efficiently separated from the 8-NHR quinoline formed without expensive or time consuming purification steps. The reaction may be carried out in the presence of a solvent such as an alcohol.

  一种改进的方法用于从8-氨基喹啉制备8-NHR喹啉。该方法包括在存在沸点为80度至90度的胺的情况下，将8-氨基喹啉与取代烷基卤化物反应。胺起到酸受体的作用，从而形成的胺盐可以在无需昂贵或耗时的纯化步骤的情况下有效地与形成的8-NHR喹啉分离。反应可以在存在溶剂（如醇类）的情况下进行。
• 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。
• Antimalarial activity of primaquine operates via a two-step biochemical relay
  作者：Grazia Camarda、Piyaporn Jirawatcharadech、Richard S. Priestley、Ahmed Saif、Sandra March、Michael H. L. Wong、Suet Leung、Alex B. Miller、David A. Baker、Pietro Alano、Mark J. I. Paine、Sangeeta N. Bhatia、Paul M. O’Neill、Stephen A. Ward、Giancarlo A. Biagini

  DOI：10.1038/s41467-019-11239-0

  日期：——

  Primaquine (PQ) is an essential antimalarial drug but despite being developed over 70 years ago, its mode of action is unclear. Here, we demonstrate that hydroxylated-PQ metabolites (OH-PQm) are responsible for efficacy against liver and sexual transmission stages of Plasmodium falciparum. The antimalarial activity of PQ against liver stages depends on host CYP2D6 status, whilst OH-PQm display direct, CYP2D6-independent, activity. PQ requires hepatic metabolism to exert activity against gametocyte stages. OH-PQm exert modest antimalarial efficacy against parasite gametocytes; however, potency is enhanced ca.1000 fold in the presence of cytochrome P450 NADPH:oxidoreductase (CPR) from the liver and bone marrow. Enhancement of OH-PQm efficacy is due to the direct reduction of quinoneimine metabolites by CPR with the concomitant and excessive generation of H₂O₂, leading to parasite killing. This detailed understanding of the mechanism paves the way to rationally re-designed 8-aminoquinolines with improved pharmacological profiles.

  摘要： 盐酸伯氨喹（PQ）是一种重要的抗疟药，但尽管已经开发了70多年，其作用方式仍不清楚。在这里，我们证明羟基化的PQ代谢物（OH-PQm）对疟原虫的肝和性传播阶段的疗效负责。PQ对肝阶段的抗疟活性取决于宿主CYP2D6状态，而OH-PQm显示出直接的、独立于CYP2D6的活性。PQ需要肝代谢才能对配子体阶段产生活性。OH-PQm对疟原虫配子体的抗疟功效较小，但在肝和骨髓的细胞色素P450 NADPH：氧化还原酶（CPR）的存在下，其效力增强约1000倍。OH-PQm功效的增强是由于CPR对醌亚胺代谢物的直接还原，同时产生大量的H₂O₂，导致疟原虫死亡。这种机制的详细理解为有理重设计具有改进药理特性的8-氨基喹啉铺平了道路。
• Elderfield et al., Journal of the American Chemical Society, 1946, vol. 68, p. 1583
  作者：Elderfield et al.

  DOI：——

  日期：——
• The Skraup Reaction with Acrolein and its Derivatives¹
  作者：Harry L. Yale、Jack Bernstein

  DOI：10.1021/ja01181a075

  日期：1948.1

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