Abstract
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, α-glucosidase and β-glucuronidase inhibiton and anticancer activity against PC-3 cell lines. Compounds 2b (IC50 = 1.3 ± 0.2 μM), 5a (IC50 = 2.3 ± 0.4 μM) and 5b (IC50 = 8.7 ± 0.1 μM) showed a potent inhibition of β-glucuronidase enzyme, more active than the standard d-saccharic acid 1,4-lactone (IC50 = 45.8 ± 2.5 μM). Compounds 5a (IC50 = 22.0 ± 0.3 μM) and 5b (IC50 = 58.4 ± 1.2 μM) were also found to be potent α-glucosidase inhibitors as compared to standard drug (acarbose, IC50 = 841 ± 1.7 μM).
Highlights
Thienothiophene derivatives possess diverse biological activities, such as antitumor, antiviral [1,2,3,4,5,6,7], and antibiotic properties
The utility of enaminone 3 in the synthesis of annelated heterocycles was further explored via its reaction with
Interesting results were obtained for pyrazole ring containing compounds 5a and 5b. Both compounds showed a potent inhibition of β-glucuronidase (5a, IC50 = 2.3 ± 0.4 and 5b IC50 = 8.7 ± 0.1 μM)
Summary
Thienothiophene derivatives possess diverse biological activities, such as antitumor, antiviral [1,2,3,4,5,6,7], and antibiotic properties. They are used as antiglaucoma drugs and as inhibitors of platelet aggregation [8,9,10,11,12]. Numerous studies have been conducted on biological profiles of thieno[2,3-b]thiophene scaffold These compounds have attracted considerable attention as moieties that offer significant synthetic advantages, such as centrosymmetry and higher rigidity. Our new results on the thieno[2,3-b]thiophene derivatives, including chemical synthesis, their in vitro antioxidant potential, α-glucosidase and β-glucuronidase inhibition, and anticancer activity against PC-3 cell lines are presented
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