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 +/- 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 IC50 = 263 +/- 0.32 mu M. In the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay, compound 2 exhibited promising activity with IC50 =33 +/- 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[l,2-b;6,5-b'] dithiophene (2) containing two chlorine substitutions exhibited more alpha-glucosidase inhibition (IC50 = 263 +/- 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.