2-(3,4-dihydroxy-benzylcarbamoyl)-8-hydroxyquinoline-7-carboxylic acid | 512539-01-4

• 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-(3,4-dihydroxy-benzylcarbamoyl)-8-hydroxyquinoline-7-carboxylic acid
• 英文别名: 2-(3,4-Dihydroxybenzylcarbamoyl)-8-hydroxyquinoline-7-carboxylic acid；2-[(3,4-dihydroxyphenyl)methylcarbamoyl]-8-hydroxyquinoline-7-carboxylic acid
• CAS: 512539-01-4
• 化学式: C₁₈H₁₄N₂O₆
• 分子量: 354.319
• InChiKey: GFYMLRYNGZEAFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 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：
  140
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(3,4-dihydroxy-benzylcarbamoyl)-8-hydroxyquinoline-7-carboxylic acid 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.17h， 生成 sodium 2-(3,4-dihydroxybenzylcarbamoyl)-8-hydroxyquinoline-7-carboxylate
  参考文献：
  名称：

  Quinoline derivatives process of synthesis and medicaments containing these derivatives

  摘要：

  该发明涉及与以下式I：1对应的衍生物：其中X是一个烷基-(CH2)n—链，其中n＝0、1或2，或O或N，Z是一个芳香族，可能包含O、N或S等杂原子作为替代物取代构成所述芳香环的碳原子，该环被取代或以其他方式与Rb取代，Rb代表1到3个取代基，选择自—OH、—OR、—COOH、—COOR、—COH、—COR、—NH2、—NH(R)、—NH(R,R′)、—SH、—SR和CN，Ra是H或—(CH2)n′—Y，其中n′＝0、1、2或3，Y和—CH3、—COOH、—COOR、—CN、—OH、—OR、SR，或一个芳基，可以选择性地用Rb取代，R和R′代表1到4C的线性或支链烷基链，及其在药学上可接受的盐中的应用作为抑制逆转录病毒整合酶的药物活性成分。

  公开号：

  US20040259911A1
• 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 吡啶 、 木榴油 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-(3,4-dihydroxy-benzylcarbamoyl)-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

• Quinoline derivatives, process of synthesis and medicaments containing these derivatives
  申请人：D'Angelo Jean

  公开号：US20060148849A1

  公开（公告）日：2006-07-06

  The invention relates to derivatives corresponding to formula I: in which X is an alkyl-(CH 2 ) n — chain with n=0, 1 or 2, or O or N, Z is an aromatic which may contain heteroatoms chosen from O, N or S, as substitutions for the carbon atoms constituting said aromatic ring, this ring being substituted or otherwise with Rb, Rb represents 1 to 3 substituents chosen from —OH, —OR, —COOH, —COOR, —COH, —COR, —NH 2 , —NH(R), —NH(R,R′), —SH, —SR and CN, Ra is H or —(CH 2 ) n′ —Y, with n′=0, 1, 2 or 3 and Y and —CH 3 , —COOH, —COOR, —CN, —OH, —OR, SR, or an aryl group optionally substituted with Rb, R and R′ represent a linear or branched alkyl chain of 1 to 4 C, and their pharmaceutically acceptable salts. Application as active ingredient of medicaments inhibiting retrovirus integrases.

  本发明涉及与式I相对应的衍生物：其中X是一个碳数为0、1或2的烷基-(CH2)n-链，或O或N，Z是一个芳香基团，可以包含O、N或S等杂原子代替构成该芳香环的碳原子，该环被取代或以其他方式与Rb取代，Rb表示1至3个取代基，选择自-OH，-OR，-COOH，-COOR，-COH，-COR，-NH2，-NH(R)，-NH(R,R')，-SH，-SR和CN，Ra是H或-(CH2)n'—Y，其中n'为0、1、2或3，Y和-CH3，-COOH，-COOR，-CN，-OH，-OR，SR或一个芳基团，可选地与Rb取代，R和R'表示1至4个碳原子的线性或支链烷基链，以及其药学上可接受的盐。本发明应用于抑制逆转录病毒整合酶的药物活性成分。
• Nitrogen-containing fused ring compound and use thereof as HIV integrase inhibitor
  申请人：Miyazaki Susumu

  公开号：US20080161311A1

  公开（公告）日：2008-07-03

  The present invention relates to a nitrogen-containing fused ring compound represented by the following formula [I] wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof, and an anti-HIV agent containing such compound. The compound of the present invention has an HIV integrase inhibitory activity, and is useful as an agent for the prophylaxis or treatment of AIDS, or as an anti-HIV agent. In addition, by the combined use with other anti-HIV agents such as a protease inhibitor, a reverse transcriptase inhibitor and the like, it can be a more effective anti-HIV agent. Because it shows integrase-specific high inhibitory activity, the compound can be a pharmaceutical agent safe on human body, which causes only a fewer side effects.

  本发明涉及一种含氮融合环化合物，其化学式如下[I]，其中每个符号如规范中定义，或其药学上可接受的盐，以及含有该化合物的抗HIV剂。本发明的化合物具有HIV整合酶抑制活性，可用作艾滋病的预防或治疗剂，或作为抗HIV剂。此外，与其他抗HIV剂如蛋白酶抑制剂、反转录酶抑制剂等联合使用，可成为更有效的抗HIV剂。由于它表现出整合酶特异性高的抑制活性，该化合物可成为一种对人体安全的药物，仅引起较少的副作用。
• 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.
• DERIVES DE QUINOLEINE, PROCEDE DE SYNTHESE, ET MEDICAMENTS RENFERMANT CES DERIVES
  申请人：BioAlliance Pharma

  公开号：EP1461319B1

  公开（公告）日：2009-04-29
• USE OF QUINOLINE DERIVATIVES WITH ANTI-INTEGRASE EFFECT AND APPLICATIONS THEREOF
  申请人：Mousnier Aurelia

  公开号：US20080161350A1

  公开（公告）日：2008-07-03

  The invention relates to the use of 8-hydroxyquinoline 7-carboxylic acid derivatives in order to produce integrase inhibiting medicaments, capable of blocking viral replication in the stages preceding integration, and if appropriate, at the level of this integration stage, these medicaments being usable for the treatment of retroviral pathologies, in particular for the treatment of AIDS.