5-(4-(dimethylamino)phenyl)-1,3,4-oxadiazole-2-thiol | 188618-61-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(4-(dimethylamino)phenyl)-1,3,4-oxadiazole-2-thiol
• 英文别名: 5-[4-(dimethylamino)phenyl]-3H-1,3,4-oxadiazole-2-thione
• CAS: 188618-61-3
• 化学式: C₁₀H₁₁N₃OS
• 分子量: 221.283
• InChiKey: ARGALKGRWHCPFE-UHFFFAOYSA-N

物化性质

• 沸点：
  317.0±44.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-(dimethylamino)phenyl)-1,3,4-oxadiazole-2-thiol 、 2-溴苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以88%的产率得到2-(5-(4-(dimethylamino)phenyl)-1,3,4-oxadiazol-2-ylthio)-1-phenylethanone
  参考文献：
  名称：

  新型2-（1,3,4-恶二唑-2-基硫基）-1-苯基乙酮衍生物的合成，生物学评价和分子对接研究

  摘要：

  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。

  DOI：

  10.1016/j.bmc.2012.03.061
• 作为产物：
  描述：

  4-二甲氨基苯甲酸甲酯 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 5-(4-(dimethylamino)phenyl)-1,3,4-oxadiazole-2-thiol
  参考文献：
  名称：

  新型2-（1,3,4-恶二唑-2-基硫基）-1-苯基乙酮衍生物的合成，生物学评价和分子对接研究

  摘要：

  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。

  DOI：

  10.1016/j.bmc.2012.03.061

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。
• Ultrasound-assisted, low-solvent and acid/base-free synthesis of 5-substituted 1,3,4-oxadiazole-2-thiols as potent antimicrobial and antioxidant agents
  作者：Elahe Yarmohammadi、Hamid Beyzaei、Reza Aryan、Ashraf Moradi

  DOI：10.1007/s11030-020-10125-y

  日期：2021.11

  broad-spectrum antimicrobial agent. Many of them displayed remarkable antioxidant properties comparable to standard controls (ascorbic acid and α-tocopherol). Synthesized 1,3,4-oxadiazoles are also potent candidates to treat cancer, Parkinson, inflammatory, and diabetes diseases. Graphic Abstract Eighteen 5-substituted 1,3,4-oxadiazole-2-thiol derivatives as potent antimicrobial and antioxidant agents were prepared

  摘要 绿色化学的目标之一是使用环保溶剂或去除和减少有害废溶剂的体积。在这项研究中，提出了一种通过芳基酰肼与 CS 2的超声辅助反应合成 5-取代的 1,3,4-恶二唑-2-硫醇衍生物的新工艺。（1:1 摩尔比）在没有碱性或酸性催化剂的情况下加入几滴 DMF。它们在易于处理和纯化的条件下以良好至极好的产率生产。为了证明所制备化合物的有效性，通过DPPH自由基清除、连续双重微量稀释和划线板法筛选了它们的抗氧化、抗菌和抗真菌潜力。用合成的杂环观察到可接受的显着抑制活性。结果表明，5-(4-fluorophenyl)-1,3,4-oxadiazole-2-thiol ( 3c ) 是一种广谱抗菌剂。其中许多显示出与标准对照（抗坏血酸和α-生育酚）。合成的 1,3,4-恶二唑也是治疗癌症、帕金森、炎症​​和糖尿病疾病的有效候选药物。 图形摘要 通过一种新的、高效的绿色工艺制备了 18 种 5-取代的
• 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.
• Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker
  作者：Jie Liu、Guang-Yu Zhang、Zhe Zhang、Bo Li、Fei Chai、Qi Wang、Zi-Dan Zhou、Ling-Ling Xu、Shou-Kai Wang、Zhen Jin、You-Zhi Tang

  DOI：10.1016/j.bioorg.2021.104956

  日期：2021.7