(E)-2-[2-(3-chlorophenyl)vinyl]quinoline-7-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-(3-chlorophenyl)vinyl]quinoline-7-carboxylic acid
• 英文别名: 2-(3-Chlorostyryl)quinoline-7-carboxylic acid；2-[(E)-2-(3-chlorophenyl)ethenyl]quinoline-7-carboxylic acid
• 化学式: C₁₈H₁₂ClNO₂
• 分子量: 309.752
• InChiKey: QAFKLMYMWZWHGZ-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氯苯甲醛 、 2-甲基-7-喹啉羧酸 在 silica gel 作用下， 反应 0.1h， 以48%的产率得到(E)-2-[2-(3-chlorophenyl)vinyl]quinoline-7-carboxylic acid
  参考文献：
  名称：

  潜在的HIV-1整合酶抑制剂的晶体结构中的分子间相互作用。

  摘要：

  获得了2-[（（2,5-二氯-4-硝基-苯基氨基）-甲氧基-甲基] -8-羟基喹啉1和2-甲基喹啉-5,8-二酮-5-肟2作为潜在的HIV -1整合酶抑制剂并通过X射线晶体学分析。还进行了能量优选构象的半经验理论计算。两种化合物的晶体结构均通过氢键和pi-pi堆积相互作用得以稳定。化合物1的平面性是由分子内的氢键引起的。

  DOI：

  10.1016/j.bmcl.2005.10.083

文献信息

• Intermolecular interactions in the crystal structures of potential HIV-1 integrase inhibitors
  作者：Katarzyna Majerz-Maniecka、Robert Musiol、Wojciech Nitek、Barbara J. Oleksyn、Jean-Francois Mouscadet、Marc Le Bret、Jaroslaw Polanski

  DOI：10.1016/j.bmcl.2005.10.083

  日期：2006.2

  8-dione-5-oxime 2 were obtained as potential HIV-1 integrase inhibitors and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred conformations were also carried out. The crystal structures of both compounds are stabilized via hydrogen bonds and pi-pi stacking interactions. The planarity of compound 1 is caused by intramolecular hydrogen bonds.

  获得了2-[（（2,5-二氯-4-硝基-苯基氨基）-甲氧基-甲基] -8-羟基喹啉1和2-甲基喹啉-5,8-二酮-5-肟2作为潜在的HIV -1整合酶抑制剂并通过X射线晶体学分析。还进行了能量优选构象的半经验理论计算。两种化合物的晶体结构均通过氢键和pi-pi堆积相互作用得以稳定。化合物1的平面性是由分子内的氢键引起的。
• 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 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.