8-hydroxyquinaldine-5-nitro-7-carboxylic acid | 934611-83-3

• 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-hydroxyquinaldine-5-nitro-7-carboxylic acid
• CAS: 934611-83-3
• 化学式: C₁₁H₈N₂O₅
• 分子量: 248.195
• InChiKey: BYJJHNWFQQHURC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  113.56
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  8-hydroxyquinaldine-5-nitro-7-carboxylic acid 、 1-(4-氟苯基)乙胺 以 二氯甲烷 为溶剂， 反应 4.0h， 以54%的产率得到N-[1-(4-fluorophenyl)ethyl]-8-hydroxy-2-methyl-5-nitroquinoline-7-carboxamide
  参考文献：
  名称：

  Investigating biological activity spectrum for novel quinoline analogues 2: Hydroxyquinolinecarboxamides with photosynthesis-inhibiting activity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.02.065
• 作为产物：
  描述：

  8-羟基喹哪啶 在 硫酸 、 硝酸 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 8-hydroxyquinaldine-5-nitro-7-carboxylic acid
  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 the antiproliferative activity of quinoline-5,8-diones and styrylquinolinecarboxylic acids on tumor cell lines
  作者：B. Podeszwa、H. Niedbala、J. Polanski、R. Musiol、D. Tabak、J. Finster、K. Serafin、M. Milczarek、J. Wietrzyk、S. Boryczka、W. Mol、J. Jampilek、J. Dohnal、D.S. Kalinowski、D.R. Richardson

  DOI：10.1016/j.bmcl.2007.09.040

  日期：2007.11

  The structure-activity relationships of new quinoline based compounds were investigated. Quinoline-5,8-dione and styrylquinoline scaffolds were used for the design of potentially active compounds. The novel analogues had comparable antiproliferative activity to cisplatin when evaluated in a bioassay against the P388 leukemia cell line. However, these compounds appeared far less efficient against SK-N-MC neuroepithelioma cells. Analogues without the 5,8-dione structure but containing the 8-carboxylic acid group were also found to induce antiproliferative activity. Hydrophobicity as measured by HPLC did not correlate with antiproliferative activity. (C) 2007 Elsevier Ltd. All rights reserved.