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Design, synthesis of coumarin tethered 1,2,3-triazoles analogues, evaluation of their antimicrobial and α-amylase inhibition activities

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Abstract

A vital transition metal Cu(II) ion catalyzed reaction was encrypted in the synthesis of new coumarin tethered triazoles 6(a-i) using the substituted azidobenzenes and substituted 3-acetyl-2H-chromen-2-ones in the presence of oxidative potassium persulfate, and DMF as a solvent and C5-H source. The structure proofs of the new compounds were provided by the spectral analysis. The in vitro antimicrobial activities of the target compounds indicate that compounds 6c and 6g of the series have potent inhibition against the tested bacteria and fungi species. Among the synthesized series compound 6g was found potent for α-amylase inhibition activity.

Graphical abstract

Synopsis. Dimethylformamide was used as a solvent and C5-H source reagent in the synthesis of triazole rings. The reaction of substituted azides, 2(a-e) and substituted 3-acetyl-2-oxo-2H-chromenes, 5(a-b) in the presence of a catalytic amount of Cu(NO3)2 and an oxidant K2S2O8 was carried out under reflux conditions using an oil bath for 36-48 h. From the reaction mixture, the target compounds 6(a-i) were extracted with ethyl acetate. The synthesized coumarin-triazole hybrids, 6(a-i) were spectroscopically characterized and evaluated for antimicrobial and α-amylase inhibitory activities.

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Acknowledgements

The authors are grateful to the IOE Instrumentation Facility, Vijnana Bhavana, University of Mysore, for spectral analysis.

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Authors and Affiliations

  1. Department of Chemistry, Yuvaraja College, University of Mysore, Mysuru, 570005, India

    VAGISH CHANNABASAPPA & AJAY KUMAR KARIYAPPA

  2. Department of Physics, School of Sciences, Jain (Deemed to be) University, Bengaluru, 560 011, India

    KARTHIK KUMARA

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  1. VAGISH CHANNABASAPPA
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Correspondence to AJAY KUMAR KARIYAPPA.

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CHANNABASAPPA, V., KUMARA, K. & KARIYAPPA, A.K. Design, synthesis of coumarin tethered 1,2,3-triazoles analogues, evaluation of their antimicrobial and α-amylase inhibition activities. J Chem Sci 133, 130 (2021). https://doi.org/10.1007/s12039-021-01997-0

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