5-bromo-6-methoxy-8-aminoquinoline | 7148-88-1

• 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: 5-bromo-6-methoxy-8-aminoquinoline
• 英文别名: 5-bromo-6-methoxy-[8]quinolylamine；5-Brom-6-methoxy-[8]chinolylamin；5-Bromo-6-methoxyquinolin-8-amine
• CAS: 7148-88-1
• 化学式: C₁₀H₉BrN₂O
• 分子量: 253.098
• InChiKey: PXAZBIOPHFDNJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-6-methoxy-8-aminoquinoline 在 硫酸 、 水 、 氢溴酸 、 sodium nitrite 、 苯酚 作用下， 生成 7-bromo-6-methoxyquinoline
  参考文献：
  名称：

  5-Bromo-6-methoxy-8-aminoquinoline and its Transformation to 7-Bromo-6-methoxy-8-aminoquinoline¹

  摘要：

  DOI：

  10.1021/ja01128a068
• 作为产物：
  描述：

  8-氨基-6-甲氧基喹啉 在 盐酸 、 溴 、 溶剂黄146 作用下， 生成 5-bromo-6-methoxy-8-aminoquinoline
  参考文献：
  名称：

  5-Bromo-6-methoxy-8-aminoquinoline and its Transformation to 7-Bromo-6-methoxy-8-aminoquinoline¹

  摘要：

  DOI：

  10.1021/ja01128a068

文献信息

• Bromo-6-methoxy-8-aminoquinolines: Preparation and 13C-NMR Assignments
  作者：James D. McChesney、S. Sarangan、Charles D. Hufford

  DOI：10.1002/jps.2600731256

  日期：1984.12

  Preparation of all possible monobromo-6-methoxy-8-aminoquinolines is reported. These materials provided an opportunity to assess the effect of bromine substitution on 13C-NMR chemical shift patterns. An explanation of the isomerization of 5-bromo-6-methoxy-8-acetamidoquinoline to 7-bromo-6-methoxy-8-aminoquinoline during hydrolysis is presented.

  据报道制备了所有可能的单溴-6-甲氧基-8-氨基喹啉。这些材料提供了一个机会来评估溴取代对13 C-NMR化学位移图的影响。解释了在水解过程中5-溴-6-甲氧基-8-乙酰氨基喹啉向7-溴-6-甲氧基-8-氨基喹啉的异构化。
• Dyeing composition comprising a cationic tertiary para-phenylenediamine and heterocyclic coupler, methods and uses
  申请人：L'OREAL

  公开号：US20040231067A1

  公开（公告）日：2004-11-25

  The subject of the present application is a dyeing composition for dyeing keratinous fibres, in particular human keratinous fibres such as hair, comprising, in an appropriate dyeing medium, at least one cationic tertiary para-phenylenediamine containing a pyrrolidine ring, and at least one particular heterocyclic coupler. The subject of the invention is also the dyeing method using this composition.

  本申请的主题是一种染色组合物，用于染色角蛋白纤维，特别是人类角蛋白纤维，如头发，包括在适当的染料介质中，至少包含一种含有吡咯烷环的阳离子第三对苯二胺，以及至少一种特定的杂环偶合剂。本发明的主题还包括使用该组合物的染色方法。
• Composition tinctoriale comprenant une paraphénylènediamine tertiaire cationique et un coupleur hétérocyclique ou un hydroxybenzamide; procédés et utilisations
  申请人：L'OREAL

  公开号：EP1428510A1

  公开（公告）日：2004-06-16

  La présente demande a pour objet une composition tinctoriale pour la teinture des fibres kératiniques, en particulier des fibres kératiniques humaines telles que les cheveux, comprenant dans un milieu de teinture approprié au moins une paraphénylènediamine tertiaire cationique contenant un noyau pyrrolidinique et au moins un coupleur hétérocyclique particulier, ou un hydroxybenzamide. L'invention a aussi pour objet le procédé de teinture mettant en oeuvre cette composition.

  本申请的目的是一种用于染色角蛋白纤维，特别是人类角蛋白纤维（如头发）的染色组合物，该组合物在合适的染色介质中包含至少一种含有吡咯烷核的阳离子叔对苯二胺和至少一种特定的杂环偶联剂或羟基苯甲酰胺。 本发明还涉及使用这种组合物的染色工艺。
• Endoperoxide-8-aminoquinoline hybrids as dual-stage antimalarial agents with enhanced metabolic stability
  作者：Rita Capela、Joana Magalhães、Daniela Miranda、Marta Machado、Margarida Sanches-Vaz、Inês S. Albuquerque、Moni Sharma、Jiri Gut、Philip J. Rosenthal、Raquel Frade、Maria J. Perry、Rui Moreira、Miguel Prudêncio、Francisca Lopes

  DOI：10.1016/j.ejmech.2018.02.048

  日期：2018.4

  Hybrid compounds may play a critical role in the context of the malaria eradication agenda, which will benefit from therapeutic tools active against the symptomatic erythrocytic stage of Plasmodium infection, and also capable of eliminating liver stage parasites, To address the need for efficient multistage antiplasmodial compounds, a small library of 1,2,4,5-tetraoxane-8-aminoquinoline hybrids, with the metabolically labile C-5 position of the 8-aminoquinoline moiety blocked with aryl groups, was synthesized and screened for antiplasmodial activity and metabolic stability. The hybrid compounds inhibited development of intra-erythrocytic forms of the multidrug-resistant Plasmodium falciparum W2 strain, with EC50 values in the nM range, and with low cytotoxicity against mammalian cells. The compounds also inhibited the development of P. berghei liver stage parasites, with the most potent compounds displaying EC50 values in the low mu M range. SAR analysis revealed that unbranched linkers between the endoperoxide and 8-aminoquinoline pharmacophores are most beneficial for dual antiplasmodial activity. Importantly, hybrids were significantly more potent than a 1:1 mixture of 8-aminoquinoline-tetraoxane, highlighting the superiority of the hybrid approach over the combination therapy. Furthermore, aryl substituents at C-5 of the 8-aminoquinoline moiety improve the compounds' metabolic stability when compared with their primaquine (i.e. C-5 unsubstituted) counterparts. Overall, this study reveals that blocking the quinoline C-5 position does not result in loss of dual-stage antimalarial activity, and that tetraoxane-8-aminoquinoline hybrids are an attractive approach to achieve elimination of exo- and intraerythrocytic parasites, thus with the potential to be used in malaria eradication campaigns. (C) 2018 Elsevier Masson SAS. All rights reserved.
• COMPOSITION DE TEINTURE D'OXYDATION DES FIBRES KERATINIQUES COMPRENANT UN ETHER DE CELLULOSE CATIONIQUE, UN METASILICATE ET DES COLORANTS D'OXYDATION, PROCEDE DE TEINTURE D'OXYDATION ET UTILISATION
  申请人：L'Oréal

  公开号：EP2182914A2

  公开（公告）日：2010-05-12