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Molecules 2016, 21(8), 977; doi:10.3390/molecules21080977

Efficient Double Suzuki Cross-Coupling Reactions of 2,5-Dibromo-3-hexylthiophene: Anti-Tumor, Haemolytic, Anti-Thrombolytic and Biofilm Inhibition Studies

1
Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan
2
International Center for Chemical and Biological Sciences, HEJ Research Institute of Chemistry, University of Karachi, Karachi 75270, Pakistan
3
Department of Chemistry, SBA School of Science & Engineering, Lahore University of Management Sciences, Sector U, DHA, Lahore Cantt. 54792, Pakistan
4
Faculty of Industrial Sciences & Technology, University Malaysia Pahang, Lebuhraya Tun Razak 26300, Kuantan Pahang, Malaysia
5
Faculty of Biotechnology and Biomolecular Sciences, University Putra Malaysia, Serdang, Selangor Darul Ehsan 43400, Malaysia
6
Botany and Microbiology Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia
7
Sustainable Energy Technologies (SET) Center, College of Engineering, King Saud University, Riyadh 11421, Saudi Arabia
*
Authors to whom correspondence should be addressed.
Academic Editor: Maria Emília de Sousa
Received: 27 May 2016 / Revised: 20 July 2016 / Accepted: 20 July 2016 / Published: 27 July 2016
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [689 KB, uploaded 27 July 2016]   |  

Abstract

The present study describes several novel 2,5-biaryl-3-hexylthiophene derivatives (3ai) synthesized via a Pd(0)-catalyzed Suzuki cross-coupling reaction in moderate to good yields. The novel compounds were also analyzed for their anti-thrombolytic, haemolytic, and biofilm inhibition activities. In addition, the anti-tumor activity was also evaluated in vitro for newly-synthesized compounds, where 3-hexyl-2,5-bis(4-(methylthio)phenyl)thiophene exhibited the best anti-tumor activity against 4T1 cells with IC50 value of 16 μM. Moreover, 2,5-bis(4-methylphenyl)-3-hexylthiophene showed the highest activity against MCF-7 cells with an IC50 value of 26.2 μM. On the other hand, the compound 2,5-bis(4-chloropheny)-3-hexylthiophene exhibited excellent biofilm inhibition activity. Furthermore, the compound 2,5-bis(3-chloro-4-fluorophenyl)-3-hexylthiophene also exhibited better anti-thrombolytic and hemolytic activity results as compared to the other newly-synthesized compounds. View Full-Text
Keywords: Suzuki cross-coupling reaction; 2,5-biaryl-3-hexylthiophene derivatives; anti-tumor; biofilm inhibition; haemolysis; anti-thrombolytic Suzuki cross-coupling reaction; 2,5-biaryl-3-hexylthiophene derivatives; anti-tumor; biofilm inhibition; haemolysis; anti-thrombolytic
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MDPI and ACS Style

Ikram, H.M.; Rasool, N.; Zubair, M.; Khan, K.M.; Abbas Chotana, G.; Akhtar, M.N.; Abu, N.; Alitheen, N.B.; Elgorban, A.M.; Rana, U.A. Efficient Double Suzuki Cross-Coupling Reactions of 2,5-Dibromo-3-hexylthiophene: Anti-Tumor, Haemolytic, Anti-Thrombolytic and Biofilm Inhibition Studies. Molecules 2016, 21, 977.

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