4-nitro-benzaldehyde-(N-p-tolyl oxime ) | 153524-58-4

• 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: 4-nitro-benzaldehyde-(N-p-tolyl oxime )
• 英文别名: 4-Nitro-benzaldehyd-(N-p-tolyl-oxim)；4-Nitro-benzaldoxim-N-p-tolylaether
• CAS: 153524-58-4；79687-76-6；130920-25-1
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: SVHGIWZDDGHNQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-nitro-benzaldehyde-(N-p-tolyl oxime ) 在 甲醇 、 氢氧化钾 作用下， 生成 4-nitro-N-p-tolyl-benzimidic acid methyl ester
  参考文献：
  名称：

  Bellavita, Gazzetta Chimica Italiana, 1940, vol. 70, p. 584,592

  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， 生成 4-nitro-benzaldehyde-(N-p-tolyl oxime )
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2011.05.027

文献信息

• Influence of the side-group at C=N bridging bond of bis-aryl Schiff bases on the wavelength of absorption maximum of ultraviolet absorption spectra
  作者：Qingqing Luo、Chao-Tun Cao、Zhongzhong Cao、Chenzhong Cao

  DOI：10.1002/poc.3550

  日期：2016.8

  methyl CH3 at carbon end and the CH=N(O) has a side‐group O atom at nitrogen end. In this work, a series of XPEAY and XPNY were synthesized, and their longest wavelength maximum λmax (nm) of ultraviolet absorption spectra were measured. Then the change regularity of the νmax (cm‐1, νmax=1/λmax) of XPEAY and XPNY were investigated, and they were compared with that of XBAY (reported by ref.26). The results

  化合物N-（亚苄基）苯胺XArCH = NArY（XBAY），N-（苯基-亚乙基）苯胺XArC（CH 3）= NArY（XPEAY）和N-苯基-α-苯基硝酮XArCH = N（O）ArY （XPNY）具有桥接基团CH = N，C（CH 3）= N和CH = N（O），其中C（CH 3）= N在碳端具有侧基甲基CH 3 = N（O）在氮端带有一个侧基O原子。在这项工作中，合成了一系列XPEAY和XPNY，并测量了它们的紫外线吸收光谱的最长波长最大值λmax（nm）。然后，ν的变化规律最大值（厘米-1，ν最大= 1 /λ最大对XPEAY和XPNY进行了调查），并与XBAY进行了比较（参考文献26报告）。结果表明：（1）XBAY与XPEAY或XPNY之间的νmax之间没有良好的线性关系。（2）在相同的一组的X-Y基团的耦合情况下，λ的分布最大XPEAYs的比XPNYs大。（3）侧基CH 3使得效
• Bamberger, Chemische Berichte, 1924, vol. 57, p. 2086
  作者：Bamberger

  DOI：——

  日期：——
• Reactions of heterocyclic cations with nitrogen-containing nucleophiles. 10. Synthesis of 3,5,7-triaryl-1,2-oxazepinium perchlorates by the reaction of 2,4,6-triarylpyrylium salts with nitrones and substituted hydroxylamines
  作者：�. A. Zvezdina、O. M. Golyanskaya、I. M. Andreeva、A. N. Popova、E. A. Medyantseva、G. N. Dorofeenko

  DOI：10.1007/bf00503546

  日期：1982.4
• Pavlenko, Z. I.; Badovskaya, L. A.; Torocheshnikov, V. N., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 965 - 969
  作者：Pavlenko, Z. I.、Badovskaya, L. A.、Torocheshnikov, V. N.、Kul'nevich V. G.

  DOI：——

  日期：——