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Design, synthesis and exploration of in silico α-amylase and α-glucosidase binding studies of pyrrolidine-appended quinoline-constrained compounds

Abstract

A series of new pyrrolidine-appended phenoxy-substituted quinoline derivatives were synthesized using 2-chloro-3-formyl quinoline. Initially, the second position of 2-chloro-3-formyl quinoline was successfully converted into various substituted phenoxy-substituted quinolines using various substituted phenols; then, its aldehyde function was reduced to its corresponding alcohols which is in turn converted into its corresponding pyrrolidine-appended phenoxy-substituted quinolines by treating it with 1-(2-chloroacetyl)pyrrolidine-2-carbonitrile. All these newly synthesized compounds were subjected to the in silico studies with the α-amylase and α-glucosidase enzymes to predict the binding affinity.

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Acknowledgements

Authors are thankful to the administration, VIT University, Vellore, India, for providing facilities to carry out research work and also thankful to SIF-Chemistry for providing NMR facility. Authors are thankful to IISc Bangalore and IIT Madras for HRMS facility. Author P. Hemanth Kumar is thankful to the VIT University for providing Research Associateship.

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Correspondence to S. Sarveswari.

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Hemanth Kumar, P., Jyothish Kumar, L., Pavithrra, G. et al. Design, synthesis and exploration of in silico α-amylase and α-glucosidase binding studies of pyrrolidine-appended quinoline-constrained compounds. Res Chem Intermed (2020). https://doi.org/10.1007/s11164-019-04068-9

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Keywords

  • Pyrrolidine-appended phenoxy-substituted quinolines
  • In silico studies
  • α-Amylase
  • α-Glucosidase
  • Acarbose