2-(2-chloroquinoline-3-yl)-3-(4-nitrophenyl)thiazolidin-4-one | 1255086-94-2

• 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: 2-(2-chloroquinoline-3-yl)-3-(4-nitrophenyl)thiazolidin-4-one
• 英文别名: 2-(2-Chloro-3-quinolyl)-3-(4-nitrophenyl)thiazolidin-4-one；2-(2-chloroquinolin-3-yl)-3-(4-nitrophenyl)-1,3-thiazolidin-4-one
• CAS: 1255086-94-2
• 化学式: C₁₈H₁₂ClN₃O₃S
• 分子量: 385.831
• InChiKey: FHNGILCCXWPXTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-chloroquinoline-3-yl)-3-(4-nitrophenyl)thiazolidin-4-one 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以68%的产率得到2-(4-nitrophenyl)-1,4-dihydro-1,4-epithiobenzo[b][1,6]naphthyridin-3(2H)-one
  参考文献：
  名称：

  通过Pd（0）催化的分子内Csp 2（芳基）-Csp 3（烷基）交叉脱卤化氢偶联反应有效合成应变硫桥化合物

  摘要：

  已经报道了一种使用钯（0）催化剂通过分子内Csp 2（芳基）-Csp 3（烷基）交叉脱卤化氢偶合反应构建各种硫桥化合物的操作简单有效的策略。该方法通过六元的palladacycles顺利进行，并成为生成C–C键的基石，从而以良好或优异的产率提供硫桥化合物。

  DOI：

  10.1016/j.tet.2020.131348
• 作为产物：
  描述：

  苯胺 在 硫酸 、 溶剂黄146 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-(2-chloroquinoline-3-yl)-3-(4-nitrophenyl)thiazolidin-4-one
  参考文献：
  名称：

  Quinoline-based azetidinone and thiazolidinone analogues as antimicrobial and antituberculosis agents

  摘要：

  New azetidinone and thiazolidinone class of bioactive agents based on quinoline nucleus have been synthesized. 2-Chloroquinoline-3-carbaldehyde reacted with various substituted amine to form the corresponding Schiff base intermediates. We have derived final azetidinone and thiazolidinone analogues from Schiff bases using chloroacetyl chloride and 2-mercaptoacetic acid, respectively. The newly synthesized analogues were then examined for their antimicrobial activity against some bacterial and fungal strains as two gram -ve bacteria (Escherichia coli MTCC 739 and Pseudomonas aeruginosa MTCC 741), two gram +ve bacteria (Staphylococcus aureus MTCC 96 and Bacillus subtilis MTCC 430), two fungal species (Aspergillus niger MTCC 282 and Candida albicans MTCC 183) as well as against Mycobacterium tuberculosis strain H37Rv to develop a novel class of bioactive agents. The results of bioassay showed that some of the newly synthesized azetidinones and thiazolidinones emerged as lead molecules with excellent MIC (mg/mL) values against mentioned microorganisms compared to standard drugs. The structure of the final analogues has been confirmed on the basis of IR, H-1 NMR, C-13 NMR, and elemental analysis.

  DOI：

  10.1007/s00044-012-0061-7

文献信息

• An efficient construction of quinoline-based hybrid scaffolds through palladium-catalyzed C S coupling
  作者：Bhavik S. Makwana、Mayur I. Morja、Kishor H. Chikhalia

  DOI：10.1016/j.tetlet.2023.154462

  日期：2023.5
• Quinoline-based azetidinone and thiazolidinone analogues as antimicrobial and antituberculosis agents
  作者：Bhupendra M. Mistry、Smita Jauhari

  DOI：10.1007/s00044-012-0061-7

  日期：2013.2

  New azetidinone and thiazolidinone class of bioactive agents based on quinoline nucleus have been synthesized. 2-Chloroquinoline-3-carbaldehyde reacted with various substituted amine to form the corresponding Schiff base intermediates. We have derived final azetidinone and thiazolidinone analogues from Schiff bases using chloroacetyl chloride and 2-mercaptoacetic acid, respectively. The newly synthesized analogues were then examined for their antimicrobial activity against some bacterial and fungal strains as two gram -ve bacteria (Escherichia coli MTCC 739 and Pseudomonas aeruginosa MTCC 741), two gram +ve bacteria (Staphylococcus aureus MTCC 96 and Bacillus subtilis MTCC 430), two fungal species (Aspergillus niger MTCC 282 and Candida albicans MTCC 183) as well as against Mycobacterium tuberculosis strain H37Rv to develop a novel class of bioactive agents. The results of bioassay showed that some of the newly synthesized azetidinones and thiazolidinones emerged as lead molecules with excellent MIC (mg/mL) values against mentioned microorganisms compared to standard drugs. The structure of the final analogues has been confirmed on the basis of IR, H-1 NMR, C-13 NMR, and elemental analysis.
• An efficient synthesis of strained thio-bridged compounds via Pd(0) catalyzed intramolecular Csp2(aryl)-Csp3(alkyl) cross dehydrohalogenative coupling reaction
  作者：Mayur I. Morja、Janki J. Patel、Prakashsingh M. Chauhan、Kishor H. Chikhalia

  DOI：10.1016/j.tet.2020.131348

  日期：2020.8

  An operationally simple and efficient strategy employing palladium(0) catalyst to construct a wide range of thiobridged compounds through intramolecular Csp2(aryl)-Csp3(alkyl) cross-dehydrohalogenative coupling reaction has been reported. This methodology proceeds smoothly through six-membered palladacycles and serving as a keystone for the generation of C–C bond to furnish thiobridged derivative in

  已经报道了一种使用钯（0）催化剂通过分子内Csp 2（芳基）-Csp 3（烷基）交叉脱卤化氢偶合反应构建各种硫桥化合物的操作简单有效的策略。该方法通过六元的palladacycles顺利进行，并成为生成C–C键的基石，从而以良好或优异的产率提供硫桥化合物。