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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

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...

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Autores principales: Ikram, Hafiz Mansoor, Rasool, Nasir, Zubair, Muhammad, Khan, Khalid Mohammed, Abbas Chotana, Ghayoor, Akhtar, Muhammad Nadeem, Abu, Nadiah, Alitheen, Noorjahan Banu, Elgorban, Abdallah Mohamed, Rana, Usman Ali
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273304/
https://www.ncbi.nlm.nih.gov/pubmed/27472312
http://dx.doi.org/10.3390/molecules21080977
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author Ikram, Hafiz Mansoor
Rasool, Nasir
Zubair, Muhammad
Khan, Khalid Mohammed
Abbas Chotana, Ghayoor
Akhtar, Muhammad Nadeem
Abu, Nadiah
Alitheen, Noorjahan Banu
Elgorban, Abdallah Mohamed
Rana, Usman Ali
author_facet Ikram, Hafiz Mansoor
Rasool, Nasir
Zubair, Muhammad
Khan, Khalid Mohammed
Abbas Chotana, Ghayoor
Akhtar, Muhammad Nadeem
Abu, Nadiah
Alitheen, Noorjahan Banu
Elgorban, Abdallah Mohamed
Rana, Usman Ali
author_sort Ikram, Hafiz Mansoor
collection PubMed
description 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 IC(50) value of 16 μM. Moreover, 2,5-bis(4-methylphenyl)-3-hexylthiophene showed the highest activity against MCF-7 cells with an IC(50) 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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spelling pubmed-62733042018-12-28 Efficient Double Suzuki Cross-Coupling Reactions of 2,5-Dibromo-3-hexylthiophene: Anti-Tumor, Haemolytic, Anti-Thrombolytic and Biofilm Inhibition Studies Ikram, Hafiz Mansoor Rasool, Nasir Zubair, Muhammad Khan, Khalid Mohammed Abbas Chotana, Ghayoor Akhtar, Muhammad Nadeem Abu, Nadiah Alitheen, Noorjahan Banu Elgorban, Abdallah Mohamed Rana, Usman Ali Molecules Article 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 IC(50) value of 16 μM. Moreover, 2,5-bis(4-methylphenyl)-3-hexylthiophene showed the highest activity against MCF-7 cells with an IC(50) 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. MDPI 2016-07-27 /pmc/articles/PMC6273304/ /pubmed/27472312 http://dx.doi.org/10.3390/molecules21080977 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Ikram, Hafiz Mansoor
Rasool, Nasir
Zubair, Muhammad
Khan, Khalid Mohammed
Abbas Chotana, Ghayoor
Akhtar, Muhammad Nadeem
Abu, Nadiah
Alitheen, Noorjahan Banu
Elgorban, Abdallah Mohamed
Rana, Usman Ali
Efficient Double Suzuki Cross-Coupling Reactions of 2,5-Dibromo-3-hexylthiophene: Anti-Tumor, Haemolytic, Anti-Thrombolytic and Biofilm Inhibition Studies
title Efficient Double Suzuki Cross-Coupling Reactions of 2,5-Dibromo-3-hexylthiophene: Anti-Tumor, Haemolytic, Anti-Thrombolytic and Biofilm Inhibition Studies
title_full Efficient Double Suzuki Cross-Coupling Reactions of 2,5-Dibromo-3-hexylthiophene: Anti-Tumor, Haemolytic, Anti-Thrombolytic and Biofilm Inhibition Studies
title_fullStr Efficient Double Suzuki Cross-Coupling Reactions of 2,5-Dibromo-3-hexylthiophene: Anti-Tumor, Haemolytic, Anti-Thrombolytic and Biofilm Inhibition Studies
title_full_unstemmed Efficient Double Suzuki Cross-Coupling Reactions of 2,5-Dibromo-3-hexylthiophene: Anti-Tumor, Haemolytic, Anti-Thrombolytic and Biofilm Inhibition Studies
title_short Efficient Double Suzuki Cross-Coupling Reactions of 2,5-Dibromo-3-hexylthiophene: Anti-Tumor, Haemolytic, Anti-Thrombolytic and Biofilm Inhibition Studies
title_sort efficient double suzuki cross-coupling reactions of 2,5-dibromo-3-hexylthiophene: anti-tumor, haemolytic, anti-thrombolytic and biofilm inhibition studies
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273304/
https://www.ncbi.nlm.nih.gov/pubmed/27472312
http://dx.doi.org/10.3390/molecules21080977
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