5-(4-isopropylphenyl)-1,3,4-oxadiazole-2-thiol | 1038309-85-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-(4-isopropylphenyl)-1,3,4-oxadiazole-2-thiol
• 英文别名: 5-[4-(Propan-2-yl)phenyl]-1,3,4-oxadiazole-2-thiol；5-(4-propan-2-ylphenyl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 1038309-85-1
• 化学式: C₁₁H₁₂N₂OS
• mdl: MFCD11201451
• 分子量: 220.295
• InChiKey: APBJYSLYRXZFJK-UHFFFAOYSA-N

物化性质

• 沸点：
  282.7±33.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  65.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-isopropylphenyl)-1,3,4-oxadiazole-2-thiol 、 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67.8%的产率得到2-(4-Isopropylphenyl)-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：

  4-异丙基苯甲酸 在 硫酸 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 35.0h， 生成 5-(4-isopropylphenyl)-1,3,4-oxadiazole-2-thiol
  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, molecular modeling and biological evaluation of 2-(benzylthio)-5-aryloxadiazole derivatives as anti-tumor agents
  作者：Kai Liu、Xiang Lu、Hong-Jia Zhang、Juan Sun、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2011.11.015

  日期：2012.1

  A series of 2-(benzylthio)-5-aryloxadiazole derivatives have been designed and synthesized, and their biological activities are also evaluated for EGFR inhibitory activity. Fourteen compounds among the twenty compounds are reported for the first time. Their chemical structures are characterized by 1H NMR, MS, and elemental analysis. Anti-proliferative and EGFR inhibition assay results have demonstrated

  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。
• 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.