N’-((2-chloroquinolin-3-yl)methylene)isonicotinohydrazide | 154255-39-7

• 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)isonicotinohydrazide
• 英文别名: N'-[(2-chloroquinolin-3-yl)methylidene]benzohydrazide；N'-((2-chloroquinolin-3-yl)methylene)benzohydrazide；3-Benzoylhydrazonomethyl-2-chloroquinoline；N-[(2-chloroquinolin-3-yl)methylideneamino]benzamide
• CAS: 154255-39-7
• 化学式: C₁₇H₁₂ClN₃O
• mdl: MFCD00807943
• 分子量: 309.755
• InChiKey: YPDKCXAAJGBTLT-UHFFFAOYSA-N

物化性质

• 熔点：
  220-223 °C(Solv: ethanol (64-17-5); N,N-dimethylformamide (68-12-2))
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N’-((2-chloroquinolin-3-yl)methylene)isonicotinohydrazide 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 4-chloro-N-(1-(2-(2-chloroquinolin-3-yl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl)ethylidene)aniline
  参考文献：
  名称：

  Synthesis, Characterization, and Antimicrobial Evaluation of Quinoline-Oxadiazole–Based Azetidinone Derivatives

  摘要：

  A series of 3-chloro-1-(aryl)-4-(2-(2-chloroquinolin-3-yl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl)-4-ethyl-azetidin-2-ones (5a-l) have been synthesized and characterized by IR, H-1 NMR, and C-13 NMR. Synthesized compounds were screened for their antimicrobial activity against different strains of bacteria (E. coli, P. aeruginosa, S. aureus, S. pyogenes, C. albicans, A. niger, and A. clavatus). On the basis of statistical analysis, it has been observed that compounds had significant correlations.

  DOI：

  10.1080/00397911.2011.580199
• 作为产物：
  描述：

  N-乙酰苯胺 在 三氯氧磷 作用下， 反应 11.75h， 生成 N’-((2-chloroquinolin-3-yl)methylene)isonicotinohydrazide
  参考文献：
  名称：

  A "green" synthesis of N-(quinoline-3-ylmethylene)benzohydrazide derivatives and their cytotoxicity activities

  摘要：

  We report some hybrid molecules based on N-(quinoline-3-ylmethylene) benzohydrazide template the synthesis of which was carried out using 2-chloroquinoline-3-carbaldehyde and a variety of substituted hydrazides in PEG 400. The "green" solvent PEG 400 was recovered and reused for several times in the present reaction and was found to be effective in terms of product yield. Some of the compounds synthesized showed significant cytotoxic activity when tested in vitro.

  DOI：

  10.1590/s0103-50532011000900017

文献信息

• Synthesis and Antimicrobial Evaluation of Novel Oxa(thia)diazolylquinolines and Oxa(thia)diazepino[7,6-b] quinolines
  作者：M. A. Khalil、O. A. El-Sayed、H. A. El-Shamy

  DOI：10.1002/ardp.19933260812

  日期：——

  series of quinoline derivatives have been prepared by cyclization of the intermediate 3[(substituted)thiocarbamoyl‐hydrazonomethyl]‐2‐chloroquinolines and 3‐aroylhydrazonomethyl‐2‐chloroquinolines: 3‐(3‐Acetyl‐5‐(substituted)‐2,3‐dihydro‐1,3, 4‐oxa(thia)diazol‐2‐yl)‐2‐chloroquinolines (4; 5), 3‐(5‐(subtituted)‐1,3,4‐oxa(thia)diazol‐2‐yl)‐2‐chloroquinolines (6; 7), and 2‐(substituted)‐1,3,4‐oxa(thia)diazepino[7

  通过中间体 3 [(取代) 硫代氨基甲酰基 - 腙甲基] -2- 氯喹啉和 3- 芳酰基腙甲基 - 2- 氯喹啉的环化反应制备了三个新型系列喹啉衍生物：3- (3 - 乙酰基 - 5- (取代) -2 , 3 - 二氢 - 1,3, 4 - oxa (thia) diazol - 2-yl) -2- chloroquinolines (4; 5), 3- (5- (subtituted) -1,3,4-oxa (thia) diazol - 2 - yl) -2 - chloroquinolines (6; 7), and 2- (已取代) -1,3,4 - oxa (thia) diazepino [7,6 - b] quinolines (8; 9)。研究了这些化合物的抗微生物活性。
• Kumar, Suresh; Bawa, Sandhya; Drabu, Sushma, Acta poloniae pharmaceutica, 2010, vol. 67, # 5, p. 567 - 573
  作者：Kumar, Suresh、Bawa, Sandhya、Drabu, Sushma、Kumar, Rajiv、Machawal, Lalit

  DOI：——

  日期：——
• Synthesis, Characterization, and Antimicrobial Evaluation of Quinoline-Oxadiazole–Based Azetidinone Derivatives
  作者：Amit M. Dodiya、Niraj R. Shihory、N. C. Desai

  DOI：10.1080/00397911.2011.580199

  日期：2012.11

  A series of 3-chloro-1-(aryl)-4-(2-(2-chloroquinolin-3-yl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl)-4-ethyl-azetidin-2-ones (5a-l) have been synthesized and characterized by IR, H-1 NMR, and C-13 NMR. Synthesized compounds were screened for their antimicrobial activity against different strains of bacteria (E. coli, P. aeruginosa, S. aureus, S. pyogenes, C. albicans, A. niger, and A. clavatus). On the basis of statistical analysis, it has been observed that compounds had significant correlations.
• A "green" synthesis of N-(quinoline-3-ylmethylene)benzohydrazide derivatives and their cytotoxicity activities
  作者：Lingam Venkata Reddy、Suresh Babu Nallapati、Syed Sultan Beevi、Lakshmi Narasu Mangamoori、Khagga Mukkanti、Sarbani Pal

  DOI：10.1590/s0103-50532011000900017

  日期：——

  We report some hybrid molecules based on N-(quinoline-3-ylmethylene) benzohydrazide template the synthesis of which was carried out using 2-chloroquinoline-3-carbaldehyde and a variety of substituted hydrazides in PEG 400. The "green" solvent PEG 400 was recovered and reused for several times in the present reaction and was found to be effective in terms of product yield. Some of the compounds synthesized showed significant cytotoxic activity when tested in vitro.