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Synthesis of Thieno[2,3-b]thiophene Containing Bis-Heterocycles-Novel Pharmacophores
Department of Chemistry, Faculty of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia
Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt
Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi 75270, Pakistan
These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 27 November 2012; in revised form: 1 February 2013 / Accepted: 18 February 2013 / Published: 12 March 2013
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).
Keywords: thienothiophene; DPPH radical scavenging activity; β-glucuronidase inhibition; α-glucosidase inhibition; cytotoxicity; cancer cell lines
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Mabkhot, Y.N.; Barakat, A.; Al-Majid, A.M.; Choudhary, M.I. Synthesis of Thieno[2,3-b]thiophene Containing Bis-Heterocycles-Novel Pharmacophores. Int. J. Mol. Sci. 2013, 14, 5712-5722.
Mabkhot YN, Barakat A, Al-Majid AM, Choudhary MI. Synthesis of Thieno[2,3-b]thiophene Containing Bis-Heterocycles-Novel Pharmacophores. International Journal of Molecular Sciences. 2013; 14(3):5712-5722.
Mabkhot, Yahia N.; Barakat, Assem; Al-Majid, Abdullah M.; Choudhary, Muhammad I. 2013. "Synthesis of Thieno[2,3-b]thiophene Containing Bis-Heterocycles-Novel Pharmacophores." Int. J. Mol. Sci. 14, no. 3: 5712-5722.