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Turkish Journal of Chemistry

DOI

10.3906/kim-1801-27

Abstract

Benzodithiophenes are heterocyclic compounds that have various medicinal and industrial applications. In the present study, halobenzodithiophene, the simplest benzofused thiophene, and its derivatives were synthesized and evaluated against alpha-glucosidase, urease, and free radical production. In the alpha-glucosidase inhibition assay, compound 2,2-bisbenzothiophne (1) exhibited potent activity with IC$_{50}$ = 135 $\pm $ 0.51 $\mu $M, while its derivative 2,7-bis(butoxycarbonyl)-3,6-dichlorobenzo[1,2-$b$;6,5-$b$']dithiophene (2) exhibited promising inhibition with IC$_{50}$ = 263 $\pm $ 0.32 $\mu $M. In the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay, compound 2 exhibited promising activity with IC$_{50}$ = 33 $\pm $ 0.42 $\mu $M, while compound 1 showed moderate inhibition in the urease inhibition assay. Molecular docking studies determined the possible interaction of benzodithiophene and alpha-glucosidase on the basis of binding energy and scoring function. Structure-activity relationship analysis revealed that compound 2,7-bis (butoxycarbonyl)-3,6-dichlorobenzo[1,2-$b$;6,5-$b$'] dithiophene (1) containing two chlorine substitutions exhibited more alpha-glucosidase inhibition (IC$_{50}$ = 263 $\pm $ .0.32 $\mu $M) than other derivatives. Moreover, compound 2,7-bis (butoxycarbonyl)-3,6-dichlorobenzo[1,2-$b$;6,5-$b$'] dithiophene (2) with two chlorine substitutions exhibited potent DPPH radical scavenging activity compared to other derivatives.

Keywords

Halobenzothiophenes, alpha-glucosidase enzyme, urease enzyme, radical scavenging assay, molecular docking, structure--activity relationship

First Page

1113

Last Page

1123

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