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Turkish Journal of Chemistry

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.

DOI

10.3906/kim-1801-27

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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