N-(4-nitrobenzylidene)-5-phenyl-1,3,4-oxadiazol-2-amine | 61820-64-2

• 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: N-(4-nitrobenzylidene)-5-phenyl-1,3,4-oxadiazol-2-amine
• 英文别名: (4-nitro-benzylidene)-(5-phenyl-[1,3,4]oxadiazol-2-yl)-amine；1-(4-nitrophenyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)methanimine
• CAS: 61820-64-2
• 化学式: C₁₅H₁₀N₄O₃
• 分子量: 294.269
• InChiKey: ZZBNNRPALBXCAW-UHFFFAOYSA-N

物化性质

• 熔点：
  236-238 °C
• 沸点：
  497.1±47.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.42
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(4-nitrobenzylidene)-5-phenyl-1,3,4-oxadiazol-2-amine 、 二苯乙烯酮 以 xylene 为溶剂， 生成 7-(4-nitro-phenyl)-2,6,6-triphenyl-6,7-dihydro-[1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one
  参考文献：
  名称：

  Addition reactions of heterocumulenes. II. 1,4-Cycloaddition reactions of diphenylketene with azadienes.

  摘要：

  二苯基酮（I）与具有-C=N-C=N-多重键系统的阿扎二烯（II-IX）反应，生成了1,4-环加成物（XI-XVIII）。1,4-环加成物（XIb、XIIb和XVIb）在四氢呋喃中与铝锂氢化物反应进行氢解，分别生成了1-丙醇衍生物（XIX、XXI和XXII）。另一方面，I与3-(对乙氧基苯亚胺基)-5-苯基异噻唑（Xb）和2-苯甲亚胺基吡啶（XXIV）反应，分别得到1-[3-(5-苯基异噻唑基)]-3,3-二苯基-4-(对乙氧基苯基)-2-氮杂环丁酮（XXIII）和1-(2-吡啶基)-3,3,4-三苯基-2-氮杂环丁酮（XXV）。

  DOI：

  10.1248/cpb.24.2532
• 作为产物：
  描述：

  苯甲醛缩氨基脲 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 N-(4-nitrobenzylidene)-5-phenyl-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  2-氨基-5-芳基-1,3,4-恶二唑衍生的席夫碱的微波辅助合成与光谱分析

  摘要：

  微波辅助合成了由2-氨基-5-取代的芳基-1,3,4-恶二唑与取代的芳族醛衍生的新席夫碱。制备的席夫碱的化学结构已通过分析和光谱方法进行了研究。

  DOI：

  10.13005/ojc/280438

文献信息

• New oxadiazoles with selective-COX-2 and EGFR dual inhibitory activity: Design, synthesis, cytotoxicity evaluation and in silico studies
  作者：Nehad A. El-Sayed、Mai S. Nour、M. Alaraby Salem、Reem K. Arafa

  DOI：10.1016/j.ejmech.2019.111693

  日期：2019.12

  subjected to cytotoxic screening against UO-31 renal cancer cell line using MTT assay. Compounds IIId, IX and XIIa displayed promising behavior by showing good anticancer activity. Moreover, kinase inhibitory assay against the tyrosine kinase EGFR was performed for the three compounds showing the highest cytotoxic activity. The tested compounds were potent against EGFR with the highest activity being observed

  新型杂环恶二唑，即。2-取代5-（4-吡啶基）-1,3,4-恶二唑，2-取代5-（3-吡啶基）-1,3,4-恶二唑和2-取代5-（苯基或4 -氯苯基-1,3,4-恶二唑被设计并合成为潜在的抗癌药。在这项研究中，由于新的治疗方法假定了与选择性COX-2抑制相关的细胞毒性作用，因此在体外评估了所有化合物的COX-1和COX-2抑制活性。结果表明，与标准消炎痛，双氯芬酸钠和塞来昔布相比，大多数衍生物均表现出对COX两种同工型的抑制作用。然后，使用MTT测定法，对九种选择的化合物（IIId，VIb，VIIc，IX，XI，XIIa，XIVa，XVIb和XVIIIb）进行针对UO-31肾癌细胞系的细胞毒性筛选。化合物IIId，IX和XIIa通过显示出良好的抗癌活性而显示出有希望的行为。此外，针对显示最高细胞毒性活性的三种化合物，进行了针对酪氨酸激酶EGFR的激酶抑制试验。所测试的化合物对EGFR有效，
• Synthesis, spectral analysis, and molecular modeling of bioactive Sn(II)-complexes with oxadiazole Schiff bases
  作者：Abdalla M. Khedr、Sudha Jadon、Vipin Kumar

  DOI：10.1080/00958972.2011.569541

  日期：2011.4.20

  Sn(II)-complexes of seven 2-amino-5-substituted-aryl-1,3,4-oxadiazole Schiff bases have been synthesized and characterized by various physico-chemical studies. Their structures have been confirmed by elemental analyses, infrared, 1H NMR, UV-Vis, and mass spectral studies as well as thermal decomposition. Conductance measurements in methanol show these complexes to be non-electrolytes, and the molecular weight determinations support the proposed molecular formulae. The molecular structures of the complexes have been optimized by CS Chem 3-D Ultra Molecular Modeling and Analysis Program showing tetrahedral geometry. The bio-efficacy of the complexes has been examined against the growth of bacteria (Escherichia coli and Staphylococcus aureus) and fungi (Aspergillus flavus and Candida albicans) invitro to evaluate their anti-microbial potential.
• Synthesis, spectral, thermal analyses, molecular modeling, and antimicrobial activities of Cu(II)-complexes with 1,3,4-oxadiazole Schiff-base derivatives
  作者：Abdalla M. Khedr、Nadia A. El-Wakiel、Sudha Jadon、Vipin Kumar

  DOI：10.1080/00958972.2011.557722

  日期：2011.3.10

  Seven Cu(II)-complexes with 2-amino-5-substituted aryl-1,3,4-oxadiazole Schiff bases are presented. The donors and possible geometries of the complexes were investigated by elemental and thermal (differential thermal analysis and thermogravimetric analysis) analyses, molar conductance, magnetic moments, IR, H-1-NMR, ESR, UV-Vis, and mass spectra. The ligands are bidentate, coordinating through the nitrogen of azomethine and the nearest nitrogen to it. The results are supported by 3-D molecular modeling of 2 using CS Chem 3-D Ultra Molecular Modeling and Analysis Program. The investigated complexes have been screened for in-vitro antibacterial (Escherichia coli and Staphylococcus aureus) and antifungal (Aspergillus flavus and Candida albicans) activities. The qualitative and quantitative antimicrobial activities prove that the complexes are very active against the tested microorganisms.