2-(4-methoxyphenyl)-5-(4-pyridyl)-1,3,4-oxadiazole | 89013-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenyl)-5-(4-pyridyl)-1,3,4-oxadiazole
• 英文别名: 2-(4-methoxyphenyl)-5-(4-pyridyl)oxadiazole；2-p-anisyl-5-(4-pyridyl)-1,3,4-oxadiazole；4-(5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl)pyridine；2-(4-methoxyphenyl)-5-pyridin-4-yl-1,3,4-oxadiazole
• CAS: 89013-88-7
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: QGXSXPVCFLKHQV-UHFFFAOYSA-N

物化性质

• 熔点：
  162-164 °C(Solv: ethanol (64-17-5))
• 沸点：
  445.6±55.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [RuCl2(benzene)]2 、 2-(4-methoxyphenyl)-5-(4-pyridyl)-1,3,4-oxadiazole 以 四氢呋喃 为溶剂， 反应 6.0h， 以4%的产率得到
  参考文献：
  名称：

  Cytotoxicity of η-areneruthenium-based molecules to glioblastoma cells and their recognition by multidrug ABC transporters

  摘要：

  A new series of amphiphilic eta(6)-areneruthenium(II) compounds containing phenylazo ligands (group I: compounds la, 1b, 2a and 2b) and phenyloxadiazole ligands (group II: compounds 3a, 3b, 4a and 4b) were synthesized and characterized for their anti-glioblastoma activity. The effects of the amphiphilic eta(6)-areneruthenium(II) complexes on the viability of three human glioblastoma cell lines, U251, U87MG and T98G, were evaluated. The azo-derivative ruthenium complexes (group I) showed high cytotoxicity to all cell lines, whilst most oxadiazole-derivative complexes (group II) were less cytotoxic, except for compound 4a. The cationic complexes 2a, 2b and 4b were more cytotoxic than the neutral complexes. Compounds 2a and 2b caused a significant reduction in the percentage of cells in the G0/G1 phase, with concomitant increases in the G2/M phase and fragmented DNA in the T98G cell line. The eta(6)-areneruthenium(11) compounds were also tested in cell lines that overexpress the multidrug ABC transporters P-gp, MRP1 and ABCG2. Compounds 2b and 4a were substrates for the P-gp protein, with resistance indexes of 8.6 and 1.9, respectively. Compound 2b was also a substrate for ABCG2 and MRP1 proteins, with lower resistance indexes (1.8 and 1.6, respectively). The contribution of multidrug ABC transporters to the cytotoxicity of compound 2b in T98G cells was evidenced, since verapamil (a characteristic inhibitor of MRP1) increased the cytotoxicity of compound 2b at concentrations up to 20 mu mol L-1, whilst GP120918 and Ko143 (specific inhibitors of P-gp and ABCG2, respectively) had no significant effect. In addition, we showed that compound 2b interacts with glutathione (GSH), which could explain its cellular efflux by MRP1. Our results showed that the amphiphilic eta(6)-areneruthenium(II) complexes are promising anti-glioblastoma compounds, especially compound 2b, which was cytotoxic for all three cell lines, although it is transported by the three main multidrug ABC transporters. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.026
• 作为产物：
  描述：

  异烟酸乙酯 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 2-(4-methoxyphenyl)-5-(4-pyridyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis of Pyridine Clubbed 2,5-Disubstituted-1,3,4-Oxadiazole Derivatives Shows Potent Antimicrobial Activity

  摘要：

  在本研究中，通过使用POCl3作为循环试剂，通过反应各种取代芳香酸和异烟肼酰胺，合成了一系列2,5-二取代-1,3,4-噁二唑类似物（4a-j），保留了吡啶基团。通过色谱数据和光谱数据分析对所有合成化合物的结构阐明。评估了合成化合物对各种ESKAPE病原体的体外抗菌活性。抗菌活性针对枯草芽孢杆菌、大肠杆菌、金黄色葡萄球菌和铜绿假单胞菌进行，而抗真菌活性则对白色念珠菌和曲霉属进行测定。所有合成化合物的体外抗菌研究结果表明，化合物4d和4f表现出与参考药物头孢克肟和依康唑相当的杀菌活性。

  DOI：

  10.2174/1570178617999201130113440

文献信息

• An Expeditious and Convenient One Pot Synthesis of 2,5-Disubstituted-1,3,4-oxadiazoles
  作者：Sabir H. Mashraqui、Shailesh G. Ghadigaonkar、Rajesh S. Kenny

  DOI：10.1081/scc-120021845

  日期：2003.1.8

  Abstract A convenient, one pot procedure is reported for the synthesis of a variety of 2,5-disubstituted-1,3,4-oxadiazoles by condensing mono-arylhydrazides with acid chlorides in HMPA solvent under the microwave heating. The yields are good to excellent, the process is rapid and does not need any added acid catalyst or dehydrating reagent.

  摘要 报道了一种方便的单锅法，通过在 HMPA 溶剂中在微波加热下将单芳基酰肼与酰氯缩合来合成各种 2,5-二取代-1,3,4-恶二唑。收率从好到极好，过程快速，无需添加任何酸催化剂或脱水剂。
• A facile procedure for the one-pot synthesis of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles
  作者：Minoo Dabiri、Peyman Salehi、Mostafa Baghbanzadeh、Mahboobeh Bahramnejad

  DOI：10.1016/j.tetlet.2006.07.127

  日期：2006.9

  Unsymmetrically 2,5-disubstituted 1,3,4-oxadiazoles were efficiently synthesized from the cyclization–oxidation reaction of acyl hydrazones. Also, the synthesis of the title compounds was achieved by the condensation of acyl hydrazides and aromatic aldehydes in the presence of ceric ammonium nitrate in dichloromethane.

  不对称的2，5-二取代的1,3,4-恶二唑是通过酰基的环化-氧化反应有效合成的。同样，标题化合物的合成是通过在硝酸铈铵中在二氯甲烷中缩合酰肼和芳族醛来实现的。
• Direct Palladium‐Catalyzed C5‐Arylation of 1,3,4‐Oxadiazoles with Aryl Chlorides Promoted by Bis(di‐isopropylphosphino) Ferrocene
  作者：Loris Gelin、Henri Sabbadin、Hélène Cattey、Paul Fleurat‐Lessard、Jean‐Cyrille Hierso、Julien Roger

  DOI：10.1002/ejoc.202400212

  日期：2024.6.3

  The palladium-catalyzed direct arylation of 1,2,4-oxadiazoles proceeds efficiently at low catalyst loading (0.5 to 1 mol %) with the decisive assistance of sterically constrained ferrocenyldiphosphane ligands. This protocol tolerates electron-donating and electron-withdrawing substituents on the (heteroaryl)aryl halide.

  在空间约束的二茂铁基二膦配体的决定性帮助下，钯催化的 1,2,4-恶二唑的直接芳基化反应在低催化剂负载量（0.5 至 1 mol %）下有效进行。该方案允许（杂芳基）芳基卤化物上的给电子和吸电子取代基。
• Hall, J. Herbert; Chien, Joseph Yuming; Kauffman, Joel M., Journal of Heterocyclic Chemistry, 1992, vol. 29, # 5, p. 1245 - 1273
  作者：Hall, J. Herbert、Chien, Joseph Yuming、Kauffman, Joel M.、Litak, Peter T.、Adams, Jeffrey K.、et al.

  DOI：——

  日期：——
• Khan; Chawla, Gita; Mueed, M. Asad, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 6, p. 1302 - 1305
  作者：Khan、Chawla, Gita、Mueed, M. Asad

  DOI：——

  日期：——