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Int. J. Mol. Sci. 2013, 14(3), 5712-5722; doi:10.3390/ijms14035712
Article

Synthesis of Thieno[2,3-b]thiophene Containing Bis-Heterocycles-Novel Pharmacophores

1,†,* , 1,2,†,* , 1,†
 and
1,3,†
1 Department of Chemistry, Faculty of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia 2 Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt 3 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 / Revised: 1 February 2013 / Accepted: 18 February 2013 / Published: 12 March 2013
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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 37. 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 thienothiophene; DPPH radical scavenging activity; β-glucuronidase inhibition; α-glucosidase inhibition; cytotoxicity; cancer cell lines
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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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.

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