5-hydroxy-2-methylquinoline-6-carboxylic acid | 934611-84-4

• 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: 5-hydroxy-2-methylquinoline-6-carboxylic acid
• 英文别名: 5-Hydroxy-2-methyl-quinoline-6-carboxylic acid
• CAS: 934611-84-4
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: VUKWLYLGIHTCKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  381.0±42.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxy-2-methylquinoline-6-carboxylic acid 在 硫酸 、 硝酸 作用下， 以53%的产率得到5-hydroxy-2-methyl-8-nitroquinoline-6-carboxylic acid
  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：

  4-氨基水杨酸 、 丁烯-2-醛 在 盐酸 、 溶剂黄146 作用下， 生成 5-hydroxy-2-methylquinoline-6-carboxylic acid
  参考文献：
  名称：

  Investigating the anti-proliferative activity of styrylazanaphthalenes and azanaphthalenediones

  摘要：

  A group of styrylazanaphthalenes and azanaphthalenediones were synthesized and tested for their anti-proliferative activity. Most of the compounds were obtained with the use of microwave-assisted synthesis. The lipophilicity of the compounds was measured by RP-HPLC and their anti-proliferative activity was assayed against the human SK-N-MC neuroepithelioma and HCT116 human colon carcinoma cell lines. Active compounds were also tested in clonogenity and comet assays. Several quinazolinone and styrylquinazoline analogues were found to have markedly greater anti-proliferative activity than desferoxamine and cis-platin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.025

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.
• Small molecule glycoconjugates with anticancer activity
  作者：Gabriela Pastuch-Gawołek、Katarzyna Malarz、Anna Mrozek-Wilczkiewicz、Marta Musioł、Maciej Serda、Barbara Czaplinska、Robert Musiol

  DOI：10.1016/j.ejmech.2016.01.061

  日期：2016.4

  Glycoconjugates are combinations of sugar moieties with organic compounds. Due to their biological resemblance, such structures often have properties that are desirable for drugs. In this study we designed and synthesised several glycoconjugates from small molecular quinolines and substituted gluco- and galactopyranosyl amines. Although the parent quinoline compounds were inactive in affordable concentrations, the glycoconjugates that were obtained appeared to be cytotoxic against cancer cells at the micromolar level. When combined with copper ions, their activity increased even further. Their mechanism of action is connected to the formation of reactive oxygen species and the intercalation of DNA. (C) 2016 Elsevier Masson SAS. All rights reserved.
• X-ray and molecular modelling in fragment-based design of three small quinoline scaffolds for HIV integrase inhibitors
  作者：Katarzyna Majerz-Maniecka、Robert Musiol、Agnieszka Skórska-Stania、Dominik Tabak、Pawel Mazur、Barbara J. Oleksyn、Jaroslaw Polanski

  DOI：10.1016/j.bmc.2011.01.045

  日期：2011.3

  Crystal structures of three small molecular scaffolds based on quinoline, 2-methylquinoline-5,8-dione, 5-hydroxy-quinaldine-6-carboxylic acid and 8-hydroxy-quinaldine-7-carboxylic acid, were characterised. 5-Hydroxy-quinaldine-6-carboxylic acid was co-crystallized with cobalt(II) chloride to form a model of divalent metal cation-ligand interactions for potential HIV integrase inhibitors. Molecular docking into active site of HIV IN was also performed on 1WKN PDB file. Selected ligand-protein interactions have been found specific for active compounds. Studied structures can be used as scaffolds in fragment-based design of new potent drugs. (C) 2011 Elsevier Ltd. All rights reserved.
• Investigating the anti-proliferative activity of styrylazanaphthalenes and azanaphthalenediones
  作者：Anna Mrozek-Wilczkiewicz、Danuta S. Kalinowski、Robert Musiol、Jacek Finster、Agnieszka Szurko、Katarzyna Serafin、Magdalena Knas、Sishir K. Kamalapuram、Zaklina Kovacevic、Josef Jampilek、Alicja Ratuszna、Joanna Rzeszowska-Wolny、Des R. Richardson、Jaroslaw Polanski

  DOI：10.1016/j.bmc.2010.02.025

  日期：2010.4

  A group of styrylazanaphthalenes and azanaphthalenediones were synthesized and tested for their anti-proliferative activity. Most of the compounds were obtained with the use of microwave-assisted synthesis. The lipophilicity of the compounds was measured by RP-HPLC and their anti-proliferative activity was assayed against the human SK-N-MC neuroepithelioma and HCT116 human colon carcinoma cell lines. Active compounds were also tested in clonogenity and comet assays. Several quinazolinone and styrylquinazoline analogues were found to have markedly greater anti-proliferative activity than desferoxamine and cis-platin. (C) 2010 Elsevier Ltd. All rights reserved.