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Efficient double Suzuki cross-coupling reactions of 2,5-dibromo-3-hexylthiophene: anti-tumor, haemolytic, anti-thrombolytic and biofilm inhibition studies


Citation

Ikram, Hafiz Mansoor and Rasool, Nasir and Zubair, Muhammad and Khan, Khalid Mohammed and Chotana, Ghayoor Abbas and Akhtar, Muhammad Nadeem and Abu, Nadiah and Alitheen, Noorjahan Banu and Elgorban, Abdallah Mohamed and Rana, Usman Ali (2016) Efficient double Suzuki cross-coupling reactions of 2,5-dibromo-3-hexylthiophene: anti-tumor, haemolytic, anti-thrombolytic and biofilm inhibition studies. Molecules, 21 (8). pp. 1-11. ISSN 1420-3049

Abstract

The present study describes several novel 2,5-biaryl-3-hexylthiophene derivatives (3a-i) 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.


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Additional Metadata

Item Type: Article
Subject: Suzuki cross-coupling reaction; 2,5-biaryl-3-hexylthiophene derivatives; Anti-tumor; Biofilm inhibition; Haemolysis; Anti-thrombolytic
Divisions: Faculty of Biotechnology and Biomolecular Sciences
DOI Number: https://doi.org/10.3390/molecules21080977
Publisher: M D P I AG
Depositing User: Nurul Ainie Mokhtar
Date Deposited: 28 Feb 2018 09:22
Last Modified: 28 Feb 2018 09:22
Altmetrics: http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.3390/molecules21080977
URI: http://psasir.upm.edu.my/id/eprint/54128
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