6-chloro-2-(4-methylphenyl)-4-quinolinecarbonyl chloride | 103914-62-1

• 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: 6-chloro-2-(4-methylphenyl)-4-quinolinecarbonyl chloride
• 英文别名: 6-Chloro-2-(4-methylphenyl)quinoline-4-carbonyl chloride
• CAS: 103914-62-1
• 化学式: C₁₇H₁₁Cl₂NO
• mdl: MFCD03421285
• 分子量: 316.186
• InChiKey: JQNFHBQUZOMYTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  475.0±45.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  6-chloro-2-(4-methylphenyl)-4-quinolinecarbonyl chloride 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 6-chloro-2-(4-methylphenyl)quinoline-4-carboxylic acid benzylidene-hydrazide
  参考文献：
  名称：

  Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: Synthesis and preliminary evaluation as antimicrobial agents

  摘要：

  A new series of 2-arylquinoline-4-carboxylic acid hydrazide-hydrazones was synthesized using an appropriate synthetic route. All the target compounds were evaluated for their in vitro antimicrobial activity against Staphylococcus aureus as an example for Gram-positive bacteria, Escherichia coli as an example for Gram-negative bacteria, and Candida albicans as a representative of fungi. The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards. Among the compounds tested, compounds having nitro substituents at the arylidene moiety showed the most potent antifungal as well as antibacterial activities against E coli. Compound 23 displayed an antifungal activity comparable to that of nystatin. However, none of the compounds demonstrated any antibacterial activity against S. aureus. Hydrophobicity of the target compounds correlated weakly with their antibacterial and antifungal activities. The most potent compounds namely, 7, 18, 19, 22, and 23 were assessed for hemolytic toxicity and found to be non-hemolytic up to a concentration of 100 mu g/mL. In addition, the most potent compound (23) was evaluated for in vitro cytotoxic activity against various cancer cell lines. This compound was found to display no cytotoxic activity but rather it induces the proliferation rate of Hep-G2 cells. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.08.022
• 作为产物：
  描述：

  6-氯-2-(4-甲基苯基)喹啉-4-羧酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 生成 6-chloro-2-(4-methylphenyl)-4-quinolinecarbonyl chloride
  参考文献：
  名称：

  4-Piperidino-2-phenylquinolines

  摘要：

  揭示的化合物的结构式为##STR1##其中：R.sup.1和R.sub.2可以相同也可以不同，每个都是氢或低碳烷基；R.sup.3和R.sup.4可以相同也可以不同，每个都是氢、卤素或低碳烷基，但R.sup.3和R.sup.4不能同时为氢。这些化合物可用作抗癫痫或抗焦虑药物。

  公开号：

  US04560692A1

文献信息

• 4-Amino-2-phenylchinoline, Verfahren und Zwischenprodukte zu deren Herstellung sowie diese enthaltende Arzneimittel
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0168812A1

  公开（公告）日：1986-01-22

  Die Verbindungen der Formel worin R' und R2 unabhängig voneinander Wasserstoff oder nieder Alkyl und R3 und R4 unabhängig voneinander Wasserstoff, Halogen oder nieder Alkyl bedeuten, mit der Auflage, dass R3 und R4 nicht gleichzeitig Wasserstoff bedeuten, sind nützlich als Antikonvulsiva und Anxiolytica. Sie können hergestellt werden durch Umsetzung entsprechender 4-Chlor-2-phenylchinoline mit entsprechenden 4-Piperidincarboxamiden oder durch Aminierung von entsprechenden freien Säuren, Säurechloriden oder Estern.

  式中的化合物 其中 R' 和 R2 独立地为氢或低级烷基，R3 和 R4 独立地为氢、卤素或低级烷基，但 R3 和 R4 不能同时为氢。它们可通过相应的 4-氯-2-苯基喹啉与相应的 4-哌啶甲酰胺反应，或通过相应的游离酸、酸氯化物或酯的胺化反应制备。
• US4560692A
  申请人：——

  公开号：US4560692A

  公开（公告）日：1985-12-24
• 4-Piperidino-2-phenylquinolines
  申请人：Hoffmann-La Roche Inc.

  公开号：US04560692A1

  公开（公告）日：1985-12-24

  Disclosed are compounds of the formula ##STR1## wherein: R.sup.1 and R.sub.2 may be either the same or different and each is hydrogen or lower alkyl; and wherein R.sup.3 and R.sup.4 may be either the same or different and each is hydrogen, halogen, or lower alkyl, with the proviso that R.sup.3 and R.sup.4 cannot both be hydrogen. These compounds are useful as anticonvulsant or anxiolytic agents.

  揭示的化合物的结构式为##STR1##其中：R.sup.1和R.sub.2可以相同也可以不同，每个都是氢或低碳烷基；R.sup.3和R.sup.4可以相同也可以不同，每个都是氢、卤素或低碳烷基，但R.sup.3和R.sup.4不能同时为氢。这些化合物可用作抗癫痫或抗焦虑药物。
• Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: Synthesis and preliminary evaluation as antimicrobial agents
  作者：Kamel A. Metwally、Lobna M. Abdel-Aziz、El-Sayed M. Lashine、Mohamed I. Husseiny、Rania H. Badawy

  DOI：10.1016/j.bmc.2006.08.022

  日期：2006.12

  A new series of 2-arylquinoline-4-carboxylic acid hydrazide-hydrazones was synthesized using an appropriate synthetic route. All the target compounds were evaluated for their in vitro antimicrobial activity against Staphylococcus aureus as an example for Gram-positive bacteria, Escherichia coli as an example for Gram-negative bacteria, and Candida albicans as a representative of fungi. The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards. Among the compounds tested, compounds having nitro substituents at the arylidene moiety showed the most potent antifungal as well as antibacterial activities against E coli. Compound 23 displayed an antifungal activity comparable to that of nystatin. However, none of the compounds demonstrated any antibacterial activity against S. aureus. Hydrophobicity of the target compounds correlated weakly with their antibacterial and antifungal activities. The most potent compounds namely, 7, 18, 19, 22, and 23 were assessed for hemolytic toxicity and found to be non-hemolytic up to a concentration of 100 mu g/mL. In addition, the most potent compound (23) was evaluated for in vitro cytotoxic activity against various cancer cell lines. This compound was found to display no cytotoxic activity but rather it induces the proliferation rate of Hep-G2 cells. (c) 2006 Elsevier Ltd. All rights reserved.