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Selective C-arylation of 2,5-dibromo-3-hexylthiophene via Suzuki cross coupling reaction and their pharmacological aspects

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...

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Main Authors: Ikram, Hafiz Mansoor, Rasool, Nasir, Ahmad, Gulraiz, Chotana, Ghayoor Abbas, Musharraf, Syed Ghulam, Zubair, Muhammad, Ali Rana, Usman, Zia-Ul-Haq, Muhammad, Jaafar, Hawa Z. E.
Format: Article
Language:English
Published: MDPI 2015
Online Access:http://psasir.upm.edu.my/id/eprint/46253/1/Selective%20C-arylation%20of%202%2C5-dibromo-3-hexylthiophene%20via%20Suzuki%20cross%20coupling%20reaction%20and%20their%20pharmacological%20aspects.pdf
http://psasir.upm.edu.my/id/eprint/46253/
https://www.mdpi.com/1420-3049/20/3/5202
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spelling my.upm.eprints.462532022-06-17T01:57:06Z http://psasir.upm.edu.my/id/eprint/46253/ Selective C-arylation of 2,5-dibromo-3-hexylthiophene via Suzuki cross coupling reaction and their pharmacological aspects Ikram, Hafiz Mansoor Rasool, Nasir Ahmad, Gulraiz Chotana, Ghayoor Abbas Musharraf, Syed Ghulam Zubair, Muhammad Ali Rana, Usman Zia-Ul-Haq, Muhammad Jaafar, Hawa Z. E. 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. MDPI 2015 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/46253/1/Selective%20C-arylation%20of%202%2C5-dibromo-3-hexylthiophene%20via%20Suzuki%20cross%20coupling%20reaction%20and%20their%20pharmacological%20aspects.pdf Ikram, Hafiz Mansoor and Rasool, Nasir and Ahmad, Gulraiz and Chotana, Ghayoor Abbas and Musharraf, Syed Ghulam and Zubair, Muhammad and Ali Rana, Usman and Zia-Ul-Haq, Muhammad and Jaafar, Hawa Z. E. (2015) Selective C-arylation of 2,5-dibromo-3-hexylthiophene via Suzuki cross coupling reaction and their pharmacological aspects. Molecules, 20 (3). pp. 5202-5214. ISSN 1420-3049 https://www.mdpi.com/1420-3049/20/3/5202 10.3390/molecules20035202
institution Universiti Putra Malaysia
building UPM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Putra Malaysia
content_source UPM Institutional Repository
url_provider http://psasir.upm.edu.my/
language English
description 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.
format Article
author Ikram, Hafiz Mansoor
Rasool, Nasir
Ahmad, Gulraiz
Chotana, Ghayoor Abbas
Musharraf, Syed Ghulam
Zubair, Muhammad
Ali Rana, Usman
Zia-Ul-Haq, Muhammad
Jaafar, Hawa Z. E.
spellingShingle Ikram, Hafiz Mansoor
Rasool, Nasir
Ahmad, Gulraiz
Chotana, Ghayoor Abbas
Musharraf, Syed Ghulam
Zubair, Muhammad
Ali Rana, Usman
Zia-Ul-Haq, Muhammad
Jaafar, Hawa Z. E.
Selective C-arylation of 2,5-dibromo-3-hexylthiophene via Suzuki cross coupling reaction and their pharmacological aspects
author_facet Ikram, Hafiz Mansoor
Rasool, Nasir
Ahmad, Gulraiz
Chotana, Ghayoor Abbas
Musharraf, Syed Ghulam
Zubair, Muhammad
Ali Rana, Usman
Zia-Ul-Haq, Muhammad
Jaafar, Hawa Z. E.
author_sort Ikram, Hafiz Mansoor
title Selective C-arylation of 2,5-dibromo-3-hexylthiophene via Suzuki cross coupling reaction and their pharmacological aspects
title_short Selective C-arylation of 2,5-dibromo-3-hexylthiophene via Suzuki cross coupling reaction and their pharmacological aspects
title_full Selective C-arylation of 2,5-dibromo-3-hexylthiophene via Suzuki cross coupling reaction and their pharmacological aspects
title_fullStr Selective C-arylation of 2,5-dibromo-3-hexylthiophene via Suzuki cross coupling reaction and their pharmacological aspects
title_full_unstemmed Selective C-arylation of 2,5-dibromo-3-hexylthiophene via Suzuki cross coupling reaction and their pharmacological aspects
title_sort selective c-arylation of 2,5-dibromo-3-hexylthiophene via suzuki cross coupling reaction and their pharmacological aspects
publisher MDPI
publishDate 2015
url http://psasir.upm.edu.my/id/eprint/46253/1/Selective%20C-arylation%20of%202%2C5-dibromo-3-hexylthiophene%20via%20Suzuki%20cross%20coupling%20reaction%20and%20their%20pharmacological%20aspects.pdf
http://psasir.upm.edu.my/id/eprint/46253/
https://www.mdpi.com/1420-3049/20/3/5202
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score 13.211869

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