2-(4-azidophenyl)-1,3-benzoxazole | 162374-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-azidophenyl)-1,3-benzoxazole
• 英文别名: 2-(4-azidophenyl)benzoxazole；2-(4-Azido-phenyl)-1,3-benzoxazole
• CAS: 162374-61-0
• 化学式: C₁₃H₈N₄O
• 分子量: 236.233
• InChiKey: ZCBVOKYGEVJDAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-azidophenyl)-1,3-benzoxazole 在 三氟甲磺酸 、 三氟乙酸 、 三氟乙酸酐 作用下， 以66%的产率得到2-[2-Amino-5-(1,3-benzoxazol-2-yl)phenyl]-4-(1,3-benzoxazol-2-yl)aniline
  参考文献：
  名称：

  Stevens, Malcolm F. G.; Shi, Dong-Fang; Castro, Angeles, Journal of the Chemical Society. Perkin transactions I, 1996, # 1, p. 83 - 94

  摘要：

  DOI：
• 作为产物：
  描述：

  对氨基苯甲醛 在 盐酸 、 lead(IV) tetraacetate 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 3.17h， 生成 2-(4-azidophenyl)-1,3-benzoxazole
  参考文献：
  名称：

  Microwave Assisted Synthesis of Benzoxazole-Triazole Hybrid Derivatives as Antimicrobial Agents

  摘要：

  一系列基于1,3-苯并噁唑的1,2,3-三唑化合物经过传统和微波辐射方法合成。微波辐射方法产率更高，反应时间更短，与使用绿色溶剂、环保反应条件的传统方法相比。所有目标化合物均通过红外光谱、1H、13C核磁共振和质谱分析进行表征。此外，这些化合物被筛选其体外抗菌活性，针对葡萄球菌、枯草芽孢杆菌、肺炎克雷伯氏菌和大肠杆菌等细菌菌株，以及曲霉、黄曲霉和镰刀孢镰刀菌等真菌。与标准药物相比，大多数化合物显示出良好至优秀的抗菌活性。

  DOI：

  10.14233/ajchem.2022.23546

文献信息

• Synthesis, photophysical characterization, CASSCF/CASPT2 calculations and CT-DNA interaction study of amino and azido benzazole analogues
  作者：Eduarda S. Gil、Cláudia B. da Silva、Pablo A. Nogara、Carolina H. da Silveira、João B.T. da Rocha、Bernardo A. Iglesias、Diogo S. Lüdtke、Paulo F.B. Gonçalves、Fabiano S. Rodembusch

  DOI：10.1016/j.molliq.2019.111938

  日期：2020.1

  violet region with a relatively large Stokes shift. The latter related to a solvent dependence. The amino derivatives presented higher values to the fluorescence quantum yields in despite of the azido analogues. DFT, TD-DFT and multiconfigurational calculations (SA-CASSCF and MS-CASPT2) were performed in order to investigate the photophysical features of these molecules, mainly on the azide derivatives,

  这项工作描述了氨基和叠氮苯并恶唑的合成和光物理研究。通过在多磷酸中邻位取代的苯胺与对氨基苯甲酸之间的缩合反应获得氨基衍生物。通过将预先制备的胺中的重氮盐与叠氮化钠反应合成相应的叠氮化物。这些化合物在UV-A区域呈现最大吸收，归因于完全自旋和对称电子跃迁的nm。所有化合物均在UV-A中向紫罗兰色区域显示出主要的荧光发射，并具有相对较大的斯托克斯位移。后者与溶剂依赖性有关。尽管有叠氮基类似物，但氨基衍生物对荧光量子产率仍具有较高的价值。DFT，为了研究这些分子的光物理特征，主要是在叠氮化物衍生物上，进行了TD-DFT和多构型计算（SA-CASSCF和MS-CASPT2），其中主要的兴趣是研究这些化合物中存在的固有荧光猝灭。从这个意义上说，观察到在叠氮化物化合物中观察到的弱荧光发射可能与S的解离特性有关。1状态到达S 1 / S 0状态之间的圆锥形交点，并通过该点通过非放射性衰变返回基态。此外，
• Benzoxazole derivatives as new generation of anti-breast cancer agents
  作者：A.- Mohsen M.E. Omar、Omaima M. AboulWafa、Mai S. El-Shoukrofy、Mai E. Amr

  DOI：10.1016/j.bioorg.2020.103593

  日期：2020.3

  New 2-substituted benzoxazole derivatives were synthesized and screened for their in vitro anti-proliferative activities against MCF-7 and MDA-MB-231 cell lines. Compounds 4b, 4d and 11c eliciting the highest activity against MCF-7 cells were further assayed for their cytotoxic activities against A431 and HCC827 cancer cells in addition to their in vitro inhibition of wild and mutated epidermal growth

  合成了新的2-取代的苯并恶唑衍生物，并筛选了它们对MCF-7和MDA-MB-231细胞系的体外抗增殖活性。除了体外抑制野生和突变的表皮生长因子受体（EGFR）酶外，进一步测定了对MCF-7细胞具有最高活性的化合物4b，4d和11c对A431和HCC827癌细胞的细胞毒性活性。化合物11c对A431细胞最有活性，它对EGFRWT表现出有效的抑制作用，而化合物4b和4d则比埃洛替尼对突变的EGFRL858R具有更高的效力。化合物4a，6c和8a对MDA-MB-231癌细胞表现出最强的细胞毒活性，其中化合物4a和6c的潜在芳香化酶（ARO）抑制剂比来曲唑稍弱。用化合物4b，4d，11c处理的MCF-7细胞和用化合物4a，6c和8a处理的MDA-MB-231细胞表现出caspase-9蛋白水平的显着过表达，并引起G1前细胞凋亡和细胞周期停滞在G2 / M期除高膜联蛋白V结合亲和力外，还表明细胞凋亡
• Synthesis and photophysics of benzazole based triazoles with amino acid-derived pendant units. Multiparametric optical sensors for BSA and CT-DNA in solution
  作者：Natalí P. Debia、Juan J.P. Rodríguez、Carolina H. da Silveira、Otavio A. Chaves、Bernardo A. Iglesias、Fabiano S. Rodembusch、Diogo S. Lüdtke

  DOI：10.1016/j.molliq.2020.113092

  日期：2020.7

  Herein we report the synthesis of a series of amino acid-derived triazoles by an organocatalytic cycloaddition reaction between azides and carbonyl compounds, catalyzed by a simple amine.These compounds present absorption maxima located in the UV-B ascribed to fully spin and symmetry allowed electronic transitions and a main fluorescence emission in the UV-A (similar to 380 nm) with a relatively large Stokes shift (5700 cm(-1)). No significant solvatochromism was observed in both ground and excited states. Unexpectedly, the benzoxazole derivatives presented much higher fluorescence quantum yield values (40-80%) of compared to the sulfur analogues (3-6%). In addition, the DNA binding assays indicated that these compounds presented strong interaction with CT-DNA, which could be attributed to pi-stacking and intermolecular hydrogen-bonding. The interaction of the benzazoles with bovine serum albumin (BSA) was also investigated, where a suppression mechanism was observed. In each case, docking was performed to better understand the observed interactions. (C) 2020 Elsevier B.V. All rights reserved.
• Design, Synthesis, and Anticancer Evaluation of Tetrazole-Fused Benzoxazole Derivatives as Tubulin Binding Agents
  作者：P. Ravikumar、G. S. B. Raolji、K. Venkata Sastry、S. Kalidasu、T. Balaaraju

  DOI：10.1134/s1070363218100250

  日期：2018.10

  A novel series of tetrazole fused benzoxazole derivatives 9a-9j are synthesized, and their structures are characterized by H-1 and C-13 NMR, and mass spectra. The compounds 9a, 9b, 9g, 9h, and 9j demonstrate the highest activity. The compounds 9b and 9g exhibit good anticancer activity, in particular against MCF7, Hop62, and A-549 cell lines with the range of GI(50) values from <0.1 to 4.56 M. Molecular docking study is carried out for the compounds 9a-9j, according to which the compound 9b forms one hydrogen bond with THR766 with the highest docking score (-7.33). This indicates that 9b is effeciently binging to tubulin site.