quinaldine-5,8-dicarboxylic acid | 909266-85-9

• 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: quinaldine-5,8-dicarboxylic acid
• 英文别名: 2-Methylquinoline-5,8-dicarboxylic acid；2-methylquinoline-5,8-dicarboxylic acid
• CAS: 909266-85-9
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: SPXSDBLYEGUYJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  quinaldine-5,8-dicarboxylic acid 、 邻溴苯甲醛 生成 2-[(E)-2-(2-bromophenyl)ethenyl]quinoline-5,8-dicarboxylic acid
  参考文献：
  名称：

  Investigating the antiproliferative activity of quinoline-5,8-diones and styrylquinolinecarboxylic acids on tumor cell lines

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.09.040
• 作为产物：
  描述：

  2-氨基对苯二甲酸 、 丁烯-2-醛 生成 quinaldine-5,8-dicarboxylic acid
  参考文献：
  名称：

  Investigating the antiproliferative activity of quinoline-5,8-diones and styrylquinolinecarboxylic acids on tumor cell lines

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.09.040

文献信息

• Investigating biological activity spectrum for novel quinoline analogues
  作者：Robert Musiol、Josef Jampilek、Katarina Kralova、Des R. Richardson、Danuta Kalinowski、Barbara Podeszwa、Jacek Finster、Halina Niedbala、Anna Palka、Jaroslaw Polanski

  DOI：10.1016/j.bmc.2006.11.020

  日期：2007.2

  The lack of the wide spectrum of biological data is an important obstacle preventing the efficient molecular design. Quinoline derivatives are known to exhibit a variety of biological effects. lit the current publication, we tested a series of novel quinoline analogues for their photosynthesis-inhibiting activity (the inhibition of photosynthetic electron transport in spinach chloroplasts (Spinacia oleracea L.) and the reduction of chlorophyll content in Chlorella vulgaris Beij.). Moreover, antiproliferative activity was measured using SK-N-MC neuroepithelioma cell line. We described the structure-activity relationships (SAR) between the chemical structure and biological effects of the synthesized compounds. We also measured the lipophilicity of the novel compounds by means of the RP-HPLC and illustrate the relationships between the RP-HPLC retention parameter log K (the logarithm of capacity factor K) and log P data calculated by available programs. (c) 2006 Elsevier Ltd. All rights reserved.
• An Efficient Microwave-Assisted Synthesis of Structurally Diverse Styrylquinolines
  作者：Robert Musiol、Barbara Podeszwa、Jacek Finster、Halina Niedbala、Jaroslaw Polanski

  DOI：10.1007/s00706-006-0513-1

  日期：2006.9

  Aromatic aldehydes undergo condensation with quinaldines under microwave irradiation to afford structurally diverse styrylquinolines in high yields under solvent-free conditions. A comparison with the conventional method clearly indicates the advantages of the new protocol.
• 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.