2-(4-甲氧基苯基)-5-(2-吡啶基)-1,3,4-恶二唑 | 1022282-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(4-甲氧基苯基)-5-(2-吡啶基)-1,3,4-恶二唑
• 英文名称: 2-(4-methoxyphenyl)-5-(pyridin-2-yl)-1,3,4-oxadiazole
• 英文别名: 2-(4-Methoxyphenyl)-5-pyridin-2-yl-1,3,4-oxadiazole；2-(4-methoxyphenyl)-5-pyridin-2-yl-1,3,4-oxadiazole
• CAS: 1022282-78-5
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: AFNQUCXASCTUNV-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156 °C
• 沸点：
  437.9±51.0 °C(predicted)
• 密度：
  1.226±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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 、 ammonium hexafluorophosphate 、 2-(4-甲氧基苯基)-5-(2-吡啶基)-1,3,4-恶二唑 以 甲醇 为溶剂， 反应 28.0h， 以77%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：

  4-methoxy-N’-(pyridin-2-ylmethylene)benzohydrazide 在 碘 、 potassium carbonate 、 双氧水 作用下， 以 二甲基亚砜 、 水 为溶剂， 反应 5.0h， 以92%的产率得到2-(4-甲氧基苯基)-5-(2-吡啶基)-1,3,4-恶二唑
  参考文献：
  名称：

  碘催化酰基hydr的氧化环化成2,5-取代的1,3,4-恶二唑†

  摘要：

  在室温或环境温度下，在过氧化氢水溶液的存在下，使用催化量的碘，从N-芳酰基yl和N-乙酰hydr开始，开发了一种环境友好的2,5-二取代的1,3,4-恶二唑合成方法。

  DOI：

  10.1039/c3ra44897e

文献信息

• UV‐Induced 1,3,4‐Oxadiazole Formation from 5‐Substituted Tetrazoles and Carboxylic Acids in Flow
  作者：Luke Green、Keith Livingstone、Sophie Bertrand、Simon Peace、Craig Jamieson

  DOI：10.1002/chem.202002896

  日期：2020.11.20

  A range of 1,3,4‐oxadiazoles have been synthesized using a UV‐B activated flow approach starting from carboxylic acids and 5‐substituted tetrazoles. The application of UV light represents an attractive alternative to the traditional thermolytic approach and has demonstrated comparable efficiency and versatility, with a diverse substrate scope, including the incorporation of highly substituted amino

  已使用UV-B活化流动法从羧酸和5-取代的四唑合成了1,3,4-恶二唑。紫外线的应用代表了传统热解方法的一种有吸引力的替代方法，并已证明具有可比的效率和多功能性，具有多种底物范围，包括掺入高度取代的氨基酸。
• Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds <i>via</i> sp³ C–H functionalization of azaarenes
  作者：Geeta Sai Mani、Kavitha Donthiboina、Nagula Shankaraiah、Ahmed Kamal

  DOI：10.1039/c9nj03573g

  日期：——

  for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole scaffolds has been developed via sp3 C–H functionalization. Gratifyingly, this method involves oxidative amination with concomitant base-mediated cyclization of methylhetarenes and acylhydrazines by employing iodine and Cs2CO3. The key features of the present method include good functional group tolerance, a clean protocol, metal-free conditions

  通过sp 3 C–H官能化开发了一种有效的碘介导的一锅合成方案，用于合成2,5-二取代的1,3,4-恶二唑支架。令人欣慰的是，该方法涉及通过使用碘和Cs 2 CO 3进行氧化胺化反应，并伴随碱介导的甲基戊烯和酰基肼的环化反应。本方法的关键特征包括良好的官能团耐受性，清洁的方案，无金属的条件和高收率，使得该方案成为合成生物活性分子及其关键构件的有吸引力的策略。
• 10.1080/07391102.2023.2292796
  作者：Mehandi, Rabiya、Twala, Charmy、Ahmedi, Saiema、Fatima, Aysha、ul Islam, Khursheed、Rana, Manish、Sultana, Razia、Manzoor, Nikhat、Javed, Saleem、Mahfuzul Haque, Mohammad、Iqbal, Jawed、Rahisuddin、Nishat, Nahid

  DOI：10.1080/07391102.2023.2292796

  日期：——

  1,3,4-Oxadiazole-based heterocyclic analogs (3a–3m) were synthesized via cyclization of Schiff bases with substituted aldehydes in the presence of bromine and acetic acid. The structural clarificat...

  1,3,4-恶二唑基杂环类似物 (3a-3m) 通过席夫碱与取代醛在溴和乙酸存在下环化合成。结构清晰...
• Synthesis and characteristics of a europium complex using pyridyl oxadiazole derivative as a secondary ligand
  作者：Yu Liu、Bo Liang、Daili Xiao、Meixiang Zhu、Weiguo Zhu

  DOI：10.1016/j.jallcom.2008.01.135

  日期：2009.2

  A novel europium complex using 2-(4-methoxy)phenyl-5-(2-pyridyl)-1,3,4-oxadiazole as a secondary ligand was synthesized and characterized. Its thermal stability and UV absorption and photoluminescence of this europium complex, as well as its electroluminescence in polymer light-emitting devices (PLEDs) were investigated. The results show that this europium complex displayed intense UV absorption band around 350 nm and sharp red emission peaked at 612 nm with a full width at half maximum of 9 nm in chloroform. The PLEDs with this europium complex doped into a blend of poly(N-vinylcarbazole) and 5-biphenyl-2-(4-tert-butylphenyl)-1,3,4-oxadiazole exhibited a light intensity of 12 cd/m(2) at 24 V with a characteristic red emission of europium ion at 613 rim. This implies that the europium complex using the pyridyl 1,3,4-oxadiazole derivative as a secondary ligand can exhibit intense sharp emission of europium ion under opto-excitation and electric-excitation. (C) 2008 Elsevier B.V. All rights reserved.
• Cytotoxicity of η-areneruthenium-based molecules to glioblastoma cells and their recognition by multidrug ABC transporters
  作者：Jaqueline Pazinato、Otávio M. Cruz、Karine P. Naidek、Amanda R.A. Pires、Eduard Westphal、Hugo Gallardo、Hélène Baubichon-Cortay、Maria E.M. Rocha、Glaucia R. Martinez、Sheila M.B. Winnischofer、Attilio Di Pietro、Herbert Winnischofer

  DOI：10.1016/j.ejmech.2018.02.026

  日期：2018.3

  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.