C-(2-chlorophenyl)-N-(4-methylphenyl)nitrone | 105609-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: C-(2-chlorophenyl)-N-(4-methylphenyl)nitrone
• 英文别名: Benzenamine, N-[(2-chlorophenyl)methylene]-4-methyl-, N-oxide；1-(2-chlorophenyl)-N-(4-methylphenyl)methanimine oxide
• CAS: 105609-11-8
• 化学式: C₁₄H₁₂ClNO
• 分子量: 245.708
• InChiKey: GQUNLVQAVUMCOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  C-(2-chlorophenyl)-N-(4-methylphenyl)nitrone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以60%的产率得到1-(2-氯苯基)-N-(4-甲基苯基)甲亚胺
  参考文献：
  名称：

  Matharu, Balbir Kaur; Sharma; Manrao, Journal of the Indian Chemical Society, 2005, vol. 82, # 10, p. 917 - 918

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基甲苯 在 氯化铵 、 锌 作用下， 以 氯仿 、 水 为溶剂， 反应 1.25h， 生成 C-(2-chlorophenyl)-N-(4-methylphenyl)nitrone
  参考文献：
  名称：

  Synthesis and Evaluation of Novel 5-cyclohexyl-2-(4″-substitutedphenyl)-3-(2″-substitutedphenyl)4H-2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6-dione Derivatives for TheirIn VitroAntioxidant and Antibacterial Activities

  摘要：

  1,3‐Dipolar cycloaddition reactions of N‐cyclohexyl maleimide (1) with azomethine N‐oxide (2) have afforded novel isoxazolidine (3) in excellent yield. Their structures have been characterized from their IR, 1H‐NMR, 13C‐NMR, 1H,1H‐COSY, MS(ESI), and elemental analysis techniques. In vitro antibacterial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically two Gram‐positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and two Gram‐negative bacteria (Pseudomonas aeruginosa and Escherichia coli) using agar‐well diffusion assay. Some of the compounds (3a, 3k, 3n, and 3o) exhibited promising antibacterial activities. All the synthesized compounds have also been screened for their antioxidant activities and were found to be significantly active.

  DOI：

  10.1002/jhet.2543

文献信息

• Synthesis and evaluation of novel 4-[(3H,3aH,6aH)-3-phenyl)-4,6-dioxo-2-phenyldihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-yl]benzoic acid derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents
  作者：Preet Anand、Baldev Singh

  DOI：10.1016/j.bmc.2011.05.027

  日期：2012.1

  The present study was designed to synthesize and evaluate pyrrolo-isoxazole benzoic acid derivatives as potential acetylcholinesterase (AChE) inhibitors for the management of Alzheimer's disease. The synthesis of pyrrolo-isoxazole benzoic acid derivatives involved ring opening cyclization of p-aminobenzoic acid with maleic anhydride to yield maleanilic acid, which in turn afforded N-arylmaleimide via ring closed cyclization. Azomethine-N-oxides were obtained by condensation of N-arylhydroxylamine with differently substituted benzaldehydes followed by refluxing of N-arylmaleimide with differently substituted azomethine-N-oxides to pyrrolo-isoxazole benzoic acid derivatives as cis- and trans-stereoisomers. The synthesized compounds were evaluated in vitro for AChE inhibitory activity in rat brain homogenate with donepezil as standard AChE inhibitor. Thereafter, the most potent test compound was evaluated for in vitro butyrylcholinesterase inhibitory activity and in vivo memory evaluation in scopolamine (0.4 mg/kg)-induced amnesia in mice by employing Morris water maze test. All pyrrolo-isoxazole benzoic acid derivatives demonstrated potent AChE inhibitory activity. Most of compounds exhibited similar activity to donepezil and four of them (7h, 7i, 8i, and 8h, IC50 = 19.1 +/- 3 1.9-17.5 +/- 1.5 nM) displayed higher inhibitory activity as compared to donepezil (21.5 +/- 3.2 nM) with compound 8ia (IC50 = 17.5 +/- 1.5 nM) being the most active one. The test compound 8ia also ameliorated scopolamine-induced amnesia in mice in terms of restoration of time spent in target quadrant (TSTQ) and escape latency time (ELT). It may be concluded that pyrrolo-isoxazole benzoic acid derivatives may be employed as potential AChE inhibitors. (C) 2011 Published by Elsevier Ltd.
• Synthesis and Evaluation of Novel 5-cyclohexyl-2-(4″-substitutedphenyl)-3-(2″-substitutedphenyl)4<i>H</i>-2,3,3a,5,6,6a-hexahydropyrrolo[3,4-<i>d</i>]isoxazole-4,6-dione Derivatives for Their<i>In Vitro</i>Antioxidant and Antibacterial Activities
  作者：Manpreet Kaur、Anjandeep Kaur、Baldev Singh、Baljit Singh

  DOI：10.1002/jhet.2543

  日期：2017.1

  1,3‐Dipolar cycloaddition reactions of N‐cyclohexyl maleimide (1) with azomethine N‐oxide (2) have afforded novel isoxazolidine (3) in excellent yield. Their structures have been characterized from their IR, 1H‐NMR, 13C‐NMR, 1H,1H‐COSY, MS(ESI), and elemental analysis techniques. In vitro antibacterial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically two Gram‐positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and two Gram‐negative bacteria (Pseudomonas aeruginosa and Escherichia coli) using agar‐well diffusion assay. Some of the compounds (3a, 3k, 3n, and 3o) exhibited promising antibacterial activities. All the synthesized compounds have also been screened for their antioxidant activities and were found to be significantly active.
• Matharu, Balbir Kaur; Sharma; Manrao, Journal of the Indian Chemical Society, 2005, vol. 82, # 10, p. 917 - 918
  作者：Matharu, Balbir Kaur、Sharma、Manrao

  DOI：——

  日期：——