2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-5-((2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)thio)-1,3,4-oxadiazole | 1429183-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-5-((2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)thio)-1,3,4-oxadiazole
• 英文别名: 2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-5-[2-(2-methyl-5-nitroimidazol-1-yl)ethylsulfanyl]-1,3,4-oxadiazole；2-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[2-(2-methyl-5-nitroimidazol-1-yl)ethylsulfanyl]-1,3,4-oxadiazole
• CAS: 1429183-54-9
• 化学式: C₁₆H₁₅N₅O₅S
• 分子量: 389.392
• InChiKey: PPRSUIKMFIJGAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  甲硝唑 在 溴 、 sodium ethanolate 、 三氯化磷 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-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

文献信息

• 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.