N'-[(2-chloroquinolin-3-yl)methylidene]-2-phenylacetohydrazide | 154255-37-5

• 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)methylidene]-2-phenylacetohydrazide
• 英文别名: phenylacetic acid (2-chloroquinolin-3-ylmethylene)hydrazide；3-Phenylacetylhydrazonomethyl-2-chloroquinoline；N-[(2-chloroquinolin-3-yl)methylideneamino]-2-phenylacetamide
• CAS: 154255-37-5
• 化学式: C₁₈H₁₄ClN₃O
• 分子量: 323.782
• InChiKey: NGKKYRQBQLXXGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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)methylidene]-2-phenylacetohydrazide 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 反应 0.5h， 以85%的产率得到3-(5-Benzyl-1,3,4-oxadiazol-2-yl)-2-chloroquinoline
  参考文献：
  名称：

  新型 Oxa (thia) 二唑基喹啉和 Oxa (thia) diazepino [7,6-b] 喹啉的合成和抗菌评估

  摘要：

  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。

  DOI：

  10.1002/ardp.19933260812
• 作为产物：
  描述：

  苯乙酸 在 硫酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 N'-[(2-chloroquinolin-3-yl)methylidene]-2-phenylacetohydrazide
  参考文献：
  名称：

  Synthesis, antibacterial and anticancer evaluation of 5-substituted (1,3,4-oxadiazol-2-yl)quinoline

  摘要：

  2-Chloroquinoline-3-carbaldehyde (2) was synthesized via Vilsmeier-Haack method using acetanilide. Phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1H-benzimidazol-1-yl)acetohydrazide (7a-c) were synthesized using 2-[2-(phenoxy/naphthalen-1-yl/naphthalen-2-yloxy methyl)-1H-benzimidazol-1-yl]acetohydrazide (6a-c). The title compounds 2-chloro-3-{5-[(2-phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1-H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-yl}quinolone (8a-c) were prepared using chloramine-T. In the second series, (2-chloroquinolin-3-yl)methylidene]-substituted benzohydrazide (11a-i) were prepared by the reaction of 2-chloroquinoline-3-carbaldehyde (2) and an acid hydrazide (10a-i). The synthesized compounds were characterized by IR, NMR, Mass spectrometry, elemental analysis and screened for their antibacterial (serial dilution technique and disc diffusion method) and anticancer activity by NCI 60 cell screen at a single high dose (10(-5) M) on various panel/cell lines. The synthesized compounds (8a, 8c, 12a, 12b, 12c and 12h) were acting as a magic bullet against gram-positive strains of Bacillus cereus MTCC1305, and the compounds (12a, 12c and 12h) were also found to be extremely active against Klebsiella pneumonia NCTC7447. In the in vitro screen on tested cancer cell line, the compound (12d) showed 95.70 growth percent (GP) and highly active on SNB-75 (CNS cancer) and UO-31 (renal cancer) (GP = 53.35 and 64.35, respectively), and the compound (8a) showed 96.86 GP and highly active on SNB-75 (CNS cancer GP 51.27).

  DOI：

  10.1007/s00044-014-1308-2

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, antibacterial and anticancer evaluation of 5-substituted (1,3,4-oxadiazol-2-yl)quinoline
  作者：Salahuddin、Avijit Mazumder、Mohammad Shaharyar

  DOI：10.1007/s00044-014-1308-2

  日期：2015.6

  2-Chloroquinoline-3-carbaldehyde (2) was synthesized via Vilsmeier-Haack method using acetanilide. Phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1H-benzimidazol-1-yl)acetohydrazide (7a-c) were synthesized using 2-[2-(phenoxy/naphthalen-1-yl/naphthalen-2-yloxy methyl)-1H-benzimidazol-1-yl]acetohydrazide (6a-c). The title compounds 2-chloro-3-5-[(2-phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1-H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-yl}quinolone (8a-c) were prepared using chloramine-T. In the second series, (2-chloroquinolin-3-yl)methylidene]-substituted benzohydrazide (11a-i) were prepared by the reaction of 2-chloroquinoline-3-carbaldehyde (2) and an acid hydrazide (10a-i). The synthesized compounds were characterized by IR, NMR, Mass spectrometry, elemental analysis and screened for their antibacterial (serial dilution technique and disc diffusion method) and anticancer activity by NCI 60 cell screen at a single high dose (10(-5) M) on various panel/cell lines. The synthesized compounds (8a, 8c, 12a, 12b, 12c and 12h) were acting as a magic bullet against gram-positive strains of Bacillus cereus MTCC1305, and the compounds (12a, 12c and 12h) were also found to be extremely active against Klebsiella pneumonia NCTC7447. In the in vitro screen on tested cancer cell line, the compound (12d) showed 95.70 growth percent (GP) and highly active on SNB-75 (CNS cancer) and UO-31 (renal cancer) (GP = 53.35 and 64.35, respectively), and the compound (8a) showed 96.86 GP and highly active on SNB-75 (CNS cancer GP 51.27).