5-(4-ethoxy-phenyl)-[1,3,4]-oxadiazole-2-thiol | 84159-98-8

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-ethoxy-phenyl)-[1,3,4]-oxadiazole-2-thiol
• 英文别名: 5-(4-ethoxyphenyl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 84159-98-8
• 化学式: C₁₀H₁₀N₂O₂S
• mdl: MFCD06655274
• 分子量: 222.268
• InChiKey: CVOZYGITIHHWNM-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C(Solv: ethanol (64-17-5))
• 沸点：
  305.4±44.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)
• 溶解度：
  >33.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  5-(4-ethoxy-phenyl)-[1,3,4]-oxadiazole-2-thiol 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 5-(4-ethoxyphenyl)-4-amino-3-mercapto-4H-1,2,4-triazole
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Antitubercular Activity of Novel 1,2,4-Triazoles Against MDR Strain of Mycobacterium tuberculosis

  摘要：

  耐药性结核分枝杆菌多种形式的出现促使了新机制药物的探索。最近，氟康唑作为一种基于唑类的抗结核药物，因其靶向分枝杆菌细胞色素P450而受到广泛关注。在本研究中，我们设计了基于氟康唑结构的新型1,2,4-三唑衍生物，并评估了其对结核分枝杆菌H37Rv及多药耐药（MDR）分枝杆菌的体外抗结核活性。

  DOI：

  10.1007/s11094-018-1714-8
• 作为产物：
  描述：

  对乙氧基苯甲酸 在 硫酸 、 一水合肼 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 5-(4-ethoxy-phenyl)-[1,3,4]-oxadiazole-2-thiol
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Antitubercular Activity of Novel 1,2,4-Triazoles Against MDR Strain of Mycobacterium tuberculosis

  摘要：

  耐药性结核分枝杆菌多种形式的出现促使了新机制药物的探索。最近，氟康唑作为一种基于唑类的抗结核药物，因其靶向分枝杆菌细胞色素P450而受到广泛关注。在本研究中，我们设计了基于氟康唑结构的新型1,2,4-三唑衍生物，并评估了其对结核分枝杆菌H37Rv及多药耐药（MDR）分枝杆菌的体外抗结核活性。

  DOI：

  10.1007/s11094-018-1714-8

文献信息

• Synthesis, biological evaluation, and molecular docking studies of 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety as potential antitumor agents
  作者：Qing-Zhong Zheng、Xiao-Min Zhang、Ying Xu、Kui Cheng、Qing-Cai Jiao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2010.09.051

  日期：2010.11.15

  A series of new 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety were synthesized. Anti-proliferative assay results indicated that compounds 6o and 6u exhibited the most potent activity against gastric cancer cell SGC-7901, which was more potent than the positive control. Especially, compound 6o exhibited significant telomerase inhibitory activity (IC50 = 2.3 +/- 0.07 mu M), which was comparable to the positive control ethidium bromide. Docking simulation was performed to position compound 6o into the active site of telomerase (3DU6) to determine the probable binding model. (C) 2010 Elsevier Ltd. All rights reserved.
• Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents
  作者：Qian-Ru Du、Dong-Dong Li、Ya-Zhou Pi、Jing-Ran Li、Jian Sun、Fei Fang、Wei-Qing Zhong、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2013.02.008

  日期：2013.4

  A series of novel 1,3,4-oxadiazole thioether derivatives (compounds 9-44) were designed and synthesized as potential inhibitors of thymidylate synthase (TS) and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 18 bearing a nitro substituent exhibited more potent in vitro anticancer activities with IC50 values of 0.7 +/- 0.2, 30.0 +/- 1.2, 18.3 +/- 1.4 mu M, respectively, which was superior to the positive control. In the further study, it was identified as the most potent inhibitor against two kinds of TS protein (for human TS and Escherichia coli TS, IC50 values: 0.62 and 0.47 mu M, respectively) in the TS inhibition assay in vitro and the most potent antibacterial agents with MIC (minimum inhibitory concentrations) of 1.56-3.13 mu g/mL against the tested four bacterial strains. Molecular docking and 3D-QSAR study supported that compound 18 can be selected as dual antitumor/antibacterial candidate in the future study. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure–anti-mycobacterial activities
  作者：Fliur Macaev、Ghenadie Rusu、Serghei Pogrebnoi、Alexandru Gudima、Eugenia Stingaci、Ludmila Vlad、Nathaly Shvets、Fatma Kandemirli、Anatholy Dimoglo、Robert Reynolds

  DOI：10.1016/j.bmc.2005.05.011

  日期：2005.8

  The preparation of novel 5-aryt-2-thio-1,3,4-oxadiazoles 4a 41 and the computer-aided study of their in vitro anti-tubercular activity against Myeobacterium tuberculosis H(37)Rv (ATCC 27294) are reported. The average accuracy of the electronic-topological method and neural network methods applied to the activity prediction in leave-one-out cross validation is 80%. (c) 2005 Elsevier Ltd. All rights reserved.
• Upadhyay, Prabhat Kumar; Mishra, Pradeep, Journal of the Indian Chemical Society, 2018, vol. 95, # 6, p. 661 - 666
  作者：Upadhyay, Prabhat Kumar、Mishra, Pradeep

  DOI：——

  日期：——
• EID, A. I.;SAFWAT, HANY, M.;ABD-EL-GAWAD, N., EGYPT. J. PHARM. SCI., 1979, 20, N 1-4, 31-40
  作者：EID, A. I.、SAFWAT, HANY, M.、ABD-EL-GAWAD, N.

  DOI：——

  日期：——