2-chloro-3-[(phenylamino)methylene]quinoline | 170568-96-4

• 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-chloro-3-[(phenylamino)methylene]quinoline
• 英文别名: N-((2-chloroquinolin-3-yl)methylene)aniline；N-(2-Chloroquinolin-3-ylmethylene)aniline；1-(2-chloroquinolin-3-yl)-N-phenylmethanimine
• CAS: 170568-96-4
• 化学式: C₁₆H₁₁ClN₂
• 分子量: 266.73
• InChiKey: SQUWTQPTDWYKFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯乙酰氯 、 2-chloro-3-[(phenylamino)methylene]quinoline 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.5h， 以77%的产率得到3-chloro-4-(2-chloroquinoline-3-yl)-1-phenylazetidin-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
• 作为产物：
  描述：

  N-乙酰苯胺 在 硫酸 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 2-chloro-3-[(phenylamino)methylene]quinoline
  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。
• 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。
• Ibrahim, Nabila M.; Yosef; Mahran, Egyptian Journal of Chemistry, 2010, vol. 53, # 5, p. 673 - 691
  作者：Ibrahim, Nabila M.、Yosef、Mahran

  DOI：——

  日期：——
• Datta, Neela J.; Khunt, Ranjan C.; Parikh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 2, p. 433 - 435
  作者：Datta, Neela J.、Khunt, Ranjan C.、Parikh

  DOI：——

  日期：——
• An efficient carbodiimide-mediated synthesis and DNA-binding studies of novel 2-chloro/mercapto-quinoline-fused 1,3-thiazolidinones via one-pot three-component condensation
  作者：Devappa S. Lamani、K. R. Venugopala Reddy、H. S. Bhojya Naik、H. R. Prakash Naik、L. R. Naik

  DOI：10.1080/17415990903295678

  日期：2010.2

  A new and efficient method for the preparation of 2-(2-chloroquinolin-3-yl)-3-(4-methylphenyl)-1, 3-thiazolidin-4-one derivatives has been assembled by DCC:-mediated three-component one-pot reaction of amine, aldehyde, and mercaptoacetic acid. The final compounds were obtained in quantitative yields within 50min. The synthesized compounds were characterized by elemental analysis, FT-IR, 1H-NMR, and mass spectral data. The selected compounds were studied for interaction with calf thymus DNA by electronic spectra, viscosity measurements as well as thermal denaturation studies. On binding to DNA, the absorption spectrum underwent bathochromic and hypochromic shifts. The binding constant (Kb) had a value of 5.3x105M-1 for 2a and 5.8x105M-1 for 3a. The viscosity measurements indicated that the viscosity of sonicated rod-like DNA fragments increased.