3-chloro-4-(2-chloroquinoline-3-yl)-1-(m-tolyl)azetidin-2-one | 1374865-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 3-chloro-4-(2-chloroquinoline-3-yl)-1-(m-tolyl)azetidin-2-one
• 英文别名: 3-Chloro-4-(2-chloro-3-quinolyl)-1-(m-tolyl)azetidin-2-one；3-chloro-4-(2-chloroquinolin-3-yl)-1-(3-methylphenyl)azetidin-2-one
• CAS: 1374865-36-7
• 化学式: C₁₉H₁₄Cl₂N₂O
• 分子量: 357.239
• InChiKey: SOIVMOXXIBUJLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯胺 在 硫酸 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 11.5h， 生成 3-chloro-4-(2-chloroquinoline-3-yl)-1-(m-tolyl)azetidin-2-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

• 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.