2-(3-(3,4-Dihydroxybenzyl)ureido)-8-hydroxyquinoline-7-carboxylic acid

• 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: 2-(3-(3,4-Dihydroxybenzyl)ureido)-8-hydroxyquinoline-7-carboxylic acid
• 英文别名: 2-[(3,4-dihydroxyphenyl)methylcarbamoylamino]-8-hydroxyquinoline-7-carboxylic acid
• 化学式: C₁₈H₁₅N₃O₆
• 分子量: 369.334
• InChiKey: MOCKFXGGESYTHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  152
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  8-(2,2-Dimethyl-propionyloxy)-quinoline-2,7-dicarboxylic acid 7-tert-butyl ester 2-(2,5-dioxo-pyrrolidin-1-yl) ester 在 sodium azide 、 木榴油 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 2-(3-(3,4-Dihydroxybenzyl)ureido)-8-hydroxyquinoline-7-carboxylic acid
  参考文献：
  名称：

  Linker-modified quinoline derivatives targeting HIV-1 integrase: synthesis and biological activity

  摘要：

  A novel series of HIV-1 integrase inhibitors was synthesized and tested in both in vitro and ex vivo assays. These inhibitors are featured by the presence of a quinoline subunit and an ancillary aromatic ring linked by functionalized spacers such as amide, hydrazide, urea and 1-hydroxyprop-l-en-3-one moiety. Amide derivatives are the most promising ones and could serve as leads for further developments. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.005

文献信息

• Identification and structure–activity relationship of 8-hydroxy-quinoline-7-carboxylic acid derivatives as inhibitors of Pim-1 kinase
  作者：Faten Sliman、Mélina Blairvacq、Emilie Durieu、Laurent Meijer、Jordi Rodrigo、Didier Desmaële

  DOI：10.1016/j.bmcl.2010.03.061

  日期：2010.5

  Pim-1 kinase is a cytoplasmic serine/threonine kinase that controls programmed cell death by phosphorylating substrates that regulate both apotosis and cellular metabolism. A series of 2-styrylquinolines and quinoline-2-carboxamides has been identified as potent inhibitors of the Pim-1 kinase. The 8-hydroxyquinoline 7-carboxylic acid moiety appeared to be a crucial pharmacophore for activity. Molecular modeling indicated that interaction of this scaffold with Asp186 and Lys67 residues within the ATP-binding pocket might be responsible for the kinase inhibitory potency. (C) 2010 Elsevier Ltd. All rights reserved.
• Linker-modified quinoline derivatives targeting HIV-1 integrase: synthesis and biological activity
  作者：Christophe Bénard、Fatima Zouhiri、Marie Normand-Bayle、Michèle Danet、Didier Desmaële、Hervé Leh、Jean-François Mouscadet、Gladys Mbemba、Claire-Marie Thomas、Sabine Bonnenfant、Marc Le Bret、Jean d'Angelo

  DOI：10.1016/j.bmcl.2004.03.005

  日期：2004.5

  A novel series of HIV-1 integrase inhibitors was synthesized and tested in both in vitro and ex vivo assays. These inhibitors are featured by the presence of a quinoline subunit and an ancillary aromatic ring linked by functionalized spacers such as amide, hydrazide, urea and 1-hydroxyprop-l-en-3-one moiety. Amide derivatives are the most promising ones and could serve as leads for further developments. (C) 2004 Elsevier Ltd. All rights reserved.