5-(2-chloropyridin-4-yl)-3H-1,3,4-oxadiazole-2-thione | 1357083-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(2-chloropyridin-4-yl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 1357083-08-9
• 化学式: C₇H₄ClN₃OS
• 分子量: 213.647
• InChiKey: FVBNJGBAOSMKOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-chloropyridin-4-yl)-3H-1,3,4-oxadiazole-2-thione 、 1-(2-溴乙基)-2-甲基-5-硝基-1H-咪唑 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以57.5%的产率得到2-(2-Chloropyridin-4-yl)-5-((2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)thio)-1,3,4-oxadiazole
  参考文献：
  名称：

  Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2013.02.008
• 作为产物：
  描述：

  2-氯异烟酸乙酯 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 5-(2-chloropyridin-4-yl)-3H-1,3,4-oxadiazole-2-thione
  参考文献：
  名称：

  2-（苄硫基）-5-芳基恶二唑衍生物作为抗肿瘤剂的合成，分子建模和生物学评价

  摘要：

  已经设计和合成了一系列2-（苄硫基）-5-芳基恶二唑衍生物，并且还评估了它们的生物活性对EGFR的抑制活性。首次报道了二十种化合物中的十四种化合物。它们的化学结构通过1 H NMR，MS和元素分析进行表征。抗增殖和EGFR抑制测定的结果已经证实，化合物3e中示出了最有效的生物活性（IC 50  = 1.09μM为MCF-7和IC 50  = 1.51μM为EGFR）。已执行对接仿真以定位化合物3e进入EGFR活性位点以确定可能的结合模型，估计结合自由能值为-10.7 kcal / mol。在肿瘤生长抑制中具有有效抑制活性的化合物3e可能是有前途的抗肿瘤主导化合物，值得进一步研究。

  DOI：

  10.1016/j.ejmech.2011.11.015

文献信息

• Synthesis, biological evaluation and molecular docking studies of novel 2-(1,3,4-oxadiazol-2-ylthio)-1-phenylethanone derivatives
  作者：Li-Rong Zhang、Zhi-Jun Liu、Hui Zhang、Jian Sun、Yin Luo、Ting-Ting Zhao、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.03.061

  日期：2012.6

  In present study, a series of new 2-(1,3,4-oxadiazol-2-ylthio)-1-phenylethanone derivatives (6a–6x) as potential focal adhesion kinase (FAK) inhibitors were synthesized. The bioassay assays demonstrated that compound 6i showed the most potent activity, which inhibited the growth of MCF-7 and A431 cell lines with IC50 values of 140 ± 10 nM and 10 ± 1 nM, respectively. Compound 6i also exhibited significant

  在本研究中，合成了一系列新型的2-（1,3,4-恶二唑-2-基硫基）-1-苯基乙酮衍生物（6a - 6x）作为潜在的粘着斑激酶（FAK）抑制剂。生物测定表明，化合物6i表现出最强的活性，抑制了MCF-7和A431细胞系的生长，IC 50值分别为140±10 nM和10±1 nM。化合物6i还表现出显着的FAK抑制活性（IC 50  = 20±1 nM）。进行对接模拟以将化合物6i定位在FAK的活性位点中，以确定可能的结合模型。