N-((2-chloroquinolin-3-yl)methylene)-5-methylthiazol-2-amine | 1374865-48-1

• 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: N-((2-chloroquinolin-3-yl)methylene)-5-methylthiazol-2-amine
• 英文别名: 1-(2-chloroquinolin-3-yl)-N-(5-methyl-1,3-thiazol-2-yl)methanimine
• CAS: 1374865-48-1
• 化学式: C₁₄H₁₀ClN₃S
• 分子量: 287.773
• InChiKey: FMNJRBVNMMBZOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-((2-chloroquinolin-3-yl)methylene)-5-methylthiazol-2-amine 、 巯基乙酸 在 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以55%的产率得到2-(2-chloroquinolin-3-yl)-3-(5-methyl-1,3-thiazol-2-yl)-1,3-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
• 作为产物：
  描述：

  苯胺 在 硫酸 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 生成 N-((2-chloroquinolin-3-yl)methylene)-5-methylthiazol-2-amine
  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

• Synthesis and evaluation of some quinoline Schiff bases as a corrosion inhibitor for mild steel in 1 N HCl
  作者：Bhupendra M. Mistry、Smita Jauhari

  DOI：10.1007/s11164-012-0666-y

  日期：2013.3

  N-((2-chloroquinolin-3-yl)methylene)aniline (CQM) and N-((2-chloroquinolin-3-yl)methylene)-5-methylthiazol-2-amine (CQMA) were synthesized. The effect of CQM and CQMA have been investigated against mild steel (MS) in 1 N HCl solutions using conventional weight loss, potentiodynamic polarization, linear polarization, electrochemical impedance spectroscopy, UV–Vis spectroscopy and scanning electron microscopic studies. The losses in the weights of MS samples have proved that both CQM and CQMA are efficient inhibitors. The mixed mode of inhibition was confirmed by electrochemical polarizations. The adsorptions of these inhibitors are found to follow the Langmuir adsorption isotherm. CQM and CQMA adsorbs on the MS sample by chemisorptions.

  合成了N-((2-氯喹啉-3-基)亚甲基)苯胺（CQM）和N-((2-氯喹啉-3-基)亚甲基)-5-甲基噻唑-2-胺（CQMA）。研究了CQM和CQMA对1 N HCl溶液中碳钢（MS）的影响，采用了常规失重法、电位动态极化法、线性极化法、电化学阻抗谱、紫外-可见光谱和扫描电子显微镜研究。MS样品的重量损失证明CQM和CQMA都是有效的抑腐蚀剂。电化学极化确认了混合抑制模式。这些抑制剂的吸附遵循Langmuir吸附等温线。CQM和CQMA通过化学吸附在MS样品上吸附。
• 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.