(E)-2-[2-(2-hydroxyphenyl)vinyl]quinoline-5-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: (E)-2-[2-(2-hydroxyphenyl)vinyl]quinoline-5-carboxylic acid
• 英文别名: 2-(2-Hydroxystyryl)quinoline-5-carboxylic acid；2-[(E)-2-(2-hydroxyphenyl)ethenyl]quinoline-5-carboxylic acid
• 化学式: C₁₈H₁₃NO₃
• 分子量: 291.306
• InChiKey: WENQUYWLHXQUJZ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基-5-喹啉羧酸 、 邻甲基苄醇 反应 0.07h， 以70%的产率得到(E)-2-[2-(2-hydroxyphenyl)vinyl]quinoline-5-carboxylic acid
  参考文献：
  名称：

  An Efficient Microwave-Assisted Synthesis of Structurally Diverse Styrylquinolines

  摘要：

  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.

  DOI：

  10.1007/s00706-006-0513-1

文献信息

• 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.
• 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.