基于点击化学的新型对称双-1,2,3-三唑的合成、表征及生物活性
Synthesis, Characterization and Biological Activities of New Symmetric Bis-1,2,3-Triazoles with Click Chemistry.
作者信息
Celik Fatih, Unver Yasemin, Barut Burak, Ozel Arzu, Sancak Kemal
机构信息
Department of Chemistry, Karadeniz Technical University, 61080, Trabzon, Turkey.
Faculty of Pharmacy, Karadeniz Technical University, 61080, Trabzon, Turkey.
出版信息
Med Chem. 2018;14(3):230-241. doi: 10.2174/1573406413666171120165226.
BACKGROUND
1,2,3-Triazole and its derivatives have important biological activities such as antimicrobial, anti-allergic, analgesic, anti-HIV, antiinflammatory, anticancer, antimalarial and antituberculosis. Other significant triazole derivatives are 1,2,4-triazoles which play a very important role in the medicinal chemistry due to the antiinflammatory, antimicrobial, antimigraine, anticancer, antimicrobial and antimycotic activities. In this study, we aimed to synthesize a new series of bis-1,2,3-triazole derivatives including 1,2,4-triazole to obtain more effective biological activities.
METHODS
In this study, a new series of bis-1,2,3-triazole compounds (9,10,11) were synthesized. Antimicrobial Activity: Disc diffusion method was used. Enzyme Inhibition: α-Glucosidase Inhibition was investigated. Antioxidant Activities: DPPH Radical Scavenging, Phosphomolybdenum- Reducing Antioxidant Power (PRAP) and Ferrous Ion-Chelating methods were used.
RESULTS
Compounds 9a, 9c, 9e, 9f, 10a, 10b, 10d, 11a, 11b and 11f showed significant antibacterial and antifungal activity against all the strains tested. Compound 9g exhibited the highest AChE inhibition. Compounds 10f, 11a and 11g showed remarkable activity against the BuChE enzyme. Compound 10f has the highest antioxidant activities.
CONCLUSION
The compounds 9a, 9c, 9e, 9f, 10a, 10b, 10d, 11a, 11b and 11f exhibit the best antimicrobial activity against the bacteria and fungi C.albicans, Y. enterocolitica, E. coli, Candida albicans, Yersinia enterocolitica. Compound 9g exhibit the highest AChE inhibition with 72.67 ± 3.92% at 100 µg/mL. Compounds 10f, 11a and 11g showed remarkable activity against the BuChE enzyme compared to galantamine. Many of the compounds exhibited significant α-glucosidase inhibition activities. Compound 10f has the highest antioxidant activities (DPPH, PRAP, ferrous ionchelating) with 27.71 ± 0.85%, 0.689 ± 0.005, 42.07 ± 2.48 at 100 µg/mL, respectively.
背景
1,2,3 - 三唑及其衍生物具有重要的生物活性，如抗菌、抗过敏、止痛、抗HIV、抗炎、抗癌、抗疟疾和抗结核等。其他重要的三唑衍生物是1,2,4 - 三唑，由于其抗炎、抗菌、抗偏头痛、抗癌、抗菌和抗真菌活性，在药物化学中发挥着非常重要的作用。在本研究中，我们旨在合成一系列新的包含1,2,4 - 三唑的双 - 1,2,3 - 三唑衍生物，以获得更有效的生物活性。
方法
在本研究中，合成了一系列新的双 - 1,2,3 - 三唑化合物（9、10、11）。抗菌活性：采用纸片扩散法。酶抑制：研究α - 葡萄糖苷酶抑制作用。抗氧化活性：使用DPPH自由基清除法、磷钼酸还原抗氧化能力（PRAP）法和亚铁离子螯合法。
结果
化合物9a、9c、9e、9f、10a、10b、10d、11a、11b和11f对所有测试菌株均表现出显著的抗菌和抗真菌活性。化合物9g表现出最高的乙酰胆碱酯酶抑制活性。化合物10f、11a和11g对丁酰胆碱酯酶表现出显著活性。化合物10f具有最高的抗氧化活性。
结论
化合物9a、9c、9e、9f、10a、10b、10d、11a、11b和11f对白色念珠菌、小肠结肠炎耶尔森菌、大肠杆菌、白色念珠菌、小肠结肠炎耶尔森菌等细菌和真菌表现出最佳的抗菌活性。化合物9g在100μg/mL时表现出最高的乙酰胆碱酯酶抑制活性，为72.67±3.92%。与加兰他敏相比，化合物10f、11a和11g对丁酰胆碱酯酶表现出显著活性。许多化合物表现出显著的α - 葡萄糖苷酶抑制活性。化合物10f在100μg/mL时具有最高的抗氧化活性（DPPH、PRAP、亚铁离子螯合），分别为27.71±0.85%、0.689±0.005、42.07±2.48。
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