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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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