Thioenethiophene derivatives represent an important class of compounds with diverse biological activities. We describe here the synthesis of a new series of thieno[2,3-b] thiophene containing bis-heterocyclic compounds 3-7. All the compounds were evaluated for their in vitro antioxidant potential, alpha- glucosidase and beta-glucuronidase inhibiton and anticancer activity against PC-3 cell lines. Compounds 2b (IC50 = 1.3 +/- 0.2 mu M), 5a (IC50 = 2.3 +/- 0.4 mu M) and 5b (IC50 = 8.7 +/- 0.1 mu M) showed a potent inhibition of beta-glucuronidase enzyme, more active than the standard D-saccharic acid 1,4-lactone (IC50 = 45.8 +/- 2.5 mu M). Compounds 5a (IC50 = 22.0 +/- 0.3 mu M) and 5b (IC50 = 58.4 +/- 1.2 mu M) were also found to be potent a- glucosidase inhibitors as compared to standard drug (acarbose, IC50 = 841 +/- 1.7 mu M).