8-hydroxy-2-methyl-5-nitroquinoline-7-carboxylic acid-4-methoxybenzylamide | 1030596-42-9

• 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: 8-hydroxy-2-methyl-5-nitroquinoline-7-carboxylic acid-4-methoxybenzylamide
• 英文别名: 8-hydroxy-N-[(4-methoxyphenyl)methyl]-2-methyl-5-nitroquinoline-7-carboxamide
• CAS: 1030596-42-9
• 化学式: C₁₉H₁₇N₃O₅
• 分子量: 367.361
• InChiKey: ATORGAZGKVYXDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  8-羟基-2-甲基喹啉-7-羧酸 在 硫酸 、 硝酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 8-hydroxy-2-methyl-5-nitroquinoline-7-carboxylic acid-4-methoxybenzylamide
  参考文献：
  名称：

  Investigation of the Antimycobacterial Activity of 8-Hydroxyquinolines

  摘要：

  一系列基于8-羟基喹啉结构的苯乙烯喹啉和喹啉酰胺作为潜在的抗分枝杆菌药物进行了研究。通过反相高效液相色谱法（RP-HPLC）测量了这些化合物的亲脂性，并对其对卡拉福分枝杆菌、鸟分枝杆菌复合体、磨玻璃分枝杆菌、脓肿分枝杆菌、结核分枝杆菌和副结核分枝杆菌的活性进行了测试。获得的几种化合物的效果似乎优于异烟肼和环丙沙星。5,7-二硝基-8-羟基喹啉衍生物对脓肿分枝杆菌和磨玻璃分枝杆菌具有最高的效力，其效果约为环丙沙星的两倍，而2-(2-羟基苯乙烯)-8-羟基喹啉-7-羧酸与针对鸟分枝杆菌复合体的标准药物相当。讨论了结构-活性关系。

  DOI：

  10.2174/1573406410666150807111703

文献信息

• Investigating biological activity spectrum for novel quinoline analogues 2: Hydroxyquinolinecarboxamides with photosynthesis-inhibiting activity
  作者：Robert Musiol、Dominik Tabak、Halina Niedbala、Barbara Podeszwa、Josef Jampilek、Katarina Kralova、Jiri Dohnal、Jacek Finster、Agnieszka Mencel、Jaroslaw Polanski

  DOI：10.1016/j.bmc.2008.02.065

  日期：2008.4

  Two series of amides based on quinoline scaffold were designed and synthesized in search of photosynthesis inhibitors. The compounds were tested for their photosynthesis-inhibiting activity against Spinacia oleracea L. and Chlorella vulgaris Beij. The compounds lipophilicity was determined by the RP-HPLC method. Several compounds showed biological activity similar or even higher than that of the standard ( DCMU). The structure-activity relationships are discussed. (c) 2008 Elsevier Ltd. All rights reserved.
• Investigation of the Antimycobacterial Activity of 8-Hydroxyquinolines
  作者：Wioleta Cieslik、Ewelina Spaczynska、Katarzyna Malarz、Dominik Tabak、Eoghan Nevin、Jim O'Mahony、Aidan Coffey、Anna Mrozek-Wilczkiewicz、Josef Jampilek、Robert Musiol

  DOI：10.2174/1573406410666150807111703

  日期：2015.10.29

  A series of styrylquinolines and quinolineamides based on the 8-hydroxyquinoline moiety were investigated as potential antimycobacterial agents. The lipophilicity of the compounds was measured using RP-HPLC and the tests of their activity against Mycobacterium kansasii, the M. avium complex, M. smegmatis, M. abscessus, M. tuberculosis and M. avium paratuberculosis was performed. Several of the compounds that were obtained appeared to be more effective than isoniazid and ciprofloxacin. The 5,7-dinitro-8-hydroxyquinoline derivative possessed the highest potency against M. abscessus and M. Smegmatis, which was about twice as effective as ciprofloxacin, while 2-(2-hydroxystyryl)-8-hydroxyquinoline-7-carboxylic acid appeared to be comparable with the standard drugs that are against the M. avium complex. The structure activity relationships are discussed.

  一系列基于8-羟基喹啉结构的苯乙烯喹啉和喹啉酰胺作为潜在的抗分枝杆菌药物进行了研究。通过反相高效液相色谱法（RP-HPLC）测量了这些化合物的亲脂性，并对其对卡拉福分枝杆菌、鸟分枝杆菌复合体、磨玻璃分枝杆菌、脓肿分枝杆菌、结核分枝杆菌和副结核分枝杆菌的活性进行了测试。获得的几种化合物的效果似乎优于异烟肼和环丙沙星。5,7-二硝基-8-羟基喹啉衍生物对脓肿分枝杆菌和磨玻璃分枝杆菌具有最高的效力，其效果约为环丙沙星的两倍，而2-(2-羟基苯乙烯)-8-羟基喹啉-7-羧酸与针对鸟分枝杆菌复合体的标准药物相当。讨论了结构-活性关系。