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Molecules 2015, 20(3), 5202-5214; doi:10.3390/molecules20035202

Selective C-Arylation of 2,5-Dibromo-3-hexylthiophene via Suzuki Cross Coupling Reaction and Their Pharmacological Aspects

Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan
Department of Chemistry, SBA School of Science & Engineering, Lahore University of Management Sciences, Sector U, DHA, Lahore Cantt. 54792, Pakistan
International Center for Chemical and Biological Sciences, HEJ Research Institute of Chemistry, University of Karachi, Karachi 75270, Pakistan
Sustainable Energy Technologies (SET) center, College of Engineering, PO-Box 800, King Saud University, Riyadh 11421, Saudi Arabia
The Patent Office, Karachi 74200, Pakistan
Department of Crop Science, Faculty of Agriculture, University Putra Malaysia, Serdang 43400, Selangor, Malaysia
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 4 December 2014 / Revised: 6 February 2015 / Accepted: 16 February 2015 / Published: 23 March 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [865 KB, uploaded 25 March 2015]   |  


The present study reports the synthesis of various new derivatives based on 5-aryl-2-bromo-3-hexylthiophene with moderate-to-good yields via a palladium-catalyzed Suzuki cross-coupling reaction. This coupling method involved the reaction of 2,5-dibromo-3-hexylthiophene with several arylboronic acids in order to synthesize corresponding thiophene derivatives under controlled and optimal reaction conditions. The different substituents (CH3, OCH3, Cl, F etc.) present on arylboronic acids are found to have significant electronic effects on the overall properties of new products. The synthesized thiophene molecules were studied for their haemolytic, biofilm inhibition and anti-thrombolytic activities, and almost all products showed potentially good properties. The compound 2-bromo-5-(3-chloro-4-fluorophenyl)-3-hexylthiophenein particular exhibited the highest values for haemolytic and bio-film inhibition activities among all newly synthesized derivatives. In addition, the compound 2-bromo-3-hexyl-5-(4-iodophenyl)thiophene also showed high anti-thrombolytic activity, suggesting the potential medicinal applications of these newly synthesized compounds. View Full-Text
Keywords: Palladium(0); 2,5-dibromo-3-hexylthiophene; biofilm inhibition; hemolysis assay; anti-thrombolytic assay Palladium(0); 2,5-dibromo-3-hexylthiophene; biofilm inhibition; hemolysis assay; anti-thrombolytic assay

Figure 1

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. (CC BY 4.0).

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MDPI and ACS Style

Ikram, H.M.; Rasool, N.; Ahmad, G.; Chotana, G.A.; Musharraf, S.G.; Zubair, M.; Rana, U.A.; Zia-Ul-Haq, M.; Jaafar, H.Z. Selective C-Arylation of 2,5-Dibromo-3-hexylthiophene via Suzuki Cross Coupling Reaction and Their Pharmacological Aspects. Molecules 2015, 20, 5202-5214.

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