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Synthesis, Characterization and Biological Activities of New Symmetric Bis-1,2,3-Triazoles with Click Chemistry

[ Vol. 14 , Issue. 3 ]

Author(s):

Fatih Celik*, Yasemin Unver, Burak Barut, Arzu Ozel and Kemal Sancak   Pages 230 - 241 ( 12 )

Abstract:


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.

Keywords:

1, 2, 3-Triazole, anti-allergic, antimicrobial, antioxidant, click chemistry, enzyme inhibition.

Affiliation:

Department of Chemistry, Karadeniz Technical University, 61080, Trabzon, Department of Chemistry, Karadeniz Technical University, 61080, Trabzon, Faculty of Pharmacy, Karadeniz Technical University, 61080, Trabzon, Faculty of Pharmacy, Karadeniz Technical University, 61080, Trabzon, Department of Chemistry, Karadeniz Technical University, 61080, Trabzon

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