4-hydroxy-3-isopropylquinolin-2(1H)-one | 14933-32-5

• 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: 4-hydroxy-3-isopropylquinolin-2(1H)-one
• 英文别名: 4-hydroxy-3-isopropyl-1H-quinolin-2-one；3-Isopropyl-4-hydroxy-carbostyril；4-Hydroxy-3-isopropyl-1H-quinolin-2-one；4-hydroxy-3-propan-2-yl-1H-quinolin-2-one
• CAS: 14933-32-5
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: HNNFXIWBRSEYNY-UHFFFAOYSA-N

物化性质

• 沸点：
  403.4±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-isopropylquinolin-2(1H)-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以58%的产率得到4-isopropoxy-3-isopropylquinolin-2-ol
  参考文献：
  名称：

  Synthesis and anti-HIV activity of alkylated quinoline 2,4-diols

  摘要：

  Naturally occurring quinolone alkaloids, buchapine (1) and compound 2 were synthesized as reported in literature and evaluated for anti-HIV potential in human CD4+ T cell line CEM-GFP, infected with HIV-1(NL4.3) virus by p24 antigen capture ELISA assay. The compounds 1 and 2 showed potent inhibitory activity with IC50 value of 2.99 and 3.80 mu M, respectively. Further, 45 alkylated derivatives of quinoline 2,4-diol were synthesized and tested for anti-HIV potential in human CD4+ T cell line CEM-GFP. Among these, 13 derivatives have shown more than 60% inhibition. We have identified three most potent inhibitors 6, 9 and 23; compound 6 was found to be more potent than lead molecule 1 with IC50 value of 2.35 mu M and had better therapeutic index (26.64) as compared to AZT (23.07). Five derivatives 7, 19a, 19d, 21 and 24 have displayed good noticeable anti-HIV activity. All active compounds showed higher CC50 values which indicate that they have better therapeutic indices. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.015
• 作为产物：
  描述：

  2-氨基苯甲酸乙酯 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 4-hydroxy-3-isopropylquinolin-2(1H)-one
  参考文献：
  名称：

  4-Hydroxy-2-quinolones 19. A new synthesis of 3-Alkyl-2-oxo-4-hydroxyquinolines

  摘要：

  DOI：

  10.1007/bf01169841

文献信息

• Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones
  作者：Maíra Bidart de Macedo、Roman Kimmel、Damijana Urankar、Martin Gazvoda、Antonio Peixoto、Freya Cools、Eveline Torfs、Luc Verschaeve、Emerson Silva Lima、Antonín Lyčka、David Milićević、Antonín Klásek、Paul Cos、Stanislav Kafka、Janez Košmrlj、Davie Cappoen

  DOI：10.1016/j.ejmech.2017.06.061

  日期：2017.9

  None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox™ assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as

  在这项研究中，设计了一个由50个成员组成的，由4-羟基喹啉2（1 H）-取代基和两个密切相关的类似物组成的文库，对该文进行了计算机模拟评分，随后进行了合成。共有13个共有3-苯基取代基的13种衍生物对10μM以下的结核分枝杆菌H37Ra和牛分枝杆菌的抑制作用最小低于15μM的AN5A对快速生长的分枝杆菌物种无活性。在活性浓度范围内，在Vitotox™分析中，这些选择的衍生物均未显示出对MRC-5细胞具有明显的急性毒性或遗传毒性的早期迹象。结构活性研究的关系为4-羟基喹啉-2（1 H）-one支架和6-氟-4-羟基-3-苯基喹啉-2（1 H）-one（1 ）的进一步有利的取代方式提供了一些见识。38）被选为库中最有前途的成员，MIC为3.2μM，针对MRC-5的CC 50为67.4μM。
• 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
• COMPOSITION FOR OXIDATION DYEING KERATIN FIBRES COMPRISING A CATIONIC CELLULOSE ETHER, A WEAKLY OXYETHYLENATED SORBITAN FATTY ACID ESTER AND OXIDATION DYES
  申请人：L'Oréal

  公开号：EP2175830A2

  公开（公告）日：2010-04-21
• [EN] COMPOSITION FOR OXIDATION DYEING KERATIN FIBRES COMPRISING A CATIONIC CELLULOSE ETHER, A WEAKLY OXYETHYLENATED SORBITAN FATTY ACID ESTER AND OXIDATION DYES<br/>[FR] COMPOSITION DESTINÉE À LA COLORATION D'OXYDATION DE FIBRES KÉRATINIQUES, COMPRENANT UN ÉTHER CELLULOSIQUE CATIONIQUE, UN ESTER D'ACIDES GRAS ET DE SORBITAN FAIBLEMENT OXYÉTHYLÉNÉ ET DES COLORANTS D'OXYDATION
  申请人：OREAL

  公开号：WO2009016061A2

  公开（公告）日：2009-02-05

  The present invention relates to a dye composition comprising, in a medium suitable for dyeing: A) one or more particular cationic cellulose ether(s), B) one or more weakly oxyethylenated sorbitan fatty acid ester(s), and C) one or more oxidation dye(s). The present invention also relates to a process for dyeing keratin fibres using such a composition, and also to the use of this composition for dyeing keratin fibres.
• [EN] COMPOSITION OXIDATION COLOURING OF KERATINIC FIBRES, CONTAINING A CATIONIC CELLULOSE ETHER, A METASILICATE AND OXIDATION DYES, METHOD FOR OXIDATION COLOURING AND USES THEREOF<br/>[FR] 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：OREAL

  公开号：WO2009019383A2

  公开（公告）日：2009-02-12

  La présente invention concerne une composition tinctoriale comprenant, dans un milieu approprié pour la teinture : A) un ou plusieurs éther(s) de cellulose cationique(s) particulier(s), B) un ou plusieurs métasilicate(s), et C) un ou plusieurs colorant(s) d'oxydation benzénique(s), hétérocyclique(s) ou naphtalénique(s). La présente invention concerne également un procédé de teinture des fibres kératiniques mettant en oeuvre une telle composition, ainsi que l'utilisation de cette composition pour la teinture des fibres kératiniques.