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 IC50 = 135 ± µM, while its derivative 2,7-bis(butoxycarbonyl)-3,6-dichlorobenzo[1,2- b ;6,5- b ’]dithiophene (2) exhibited promising inhibition with IC50 = 263 ± µM. In the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay, compound 2 exhibited promising activity with IC50 = 33 ± µM, while compound 1 showed moderate inhibition in the urease inhibition assay. |