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Design and synthesis of arylthiophene-2-carbaldehydes via Suzuki-Miyaura reactions and their biological evaluation

A series of various novel 4-arylthiophene-2-carbaldehyde compounds were synthesized in moderate to excellent yields via Suzuki-Miyaura cross-coupling with different arylboronic pinacol esters/acids. The synthesized products were screened for their antibacterial, haemolytic, antiurease, and nitric ox...

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Main Authors: Ali, Shaukat, Rasool, Nasir, Ullah, Aman, Nasim, Faiz-ul-Hassan, Yaqoob, Asma, Zubair, Muhammad, Rashid, Umer, Riaz, Muhammad
Format: Article
Language:English
Published: MDPI 2013
Online Access:http://psasir.upm.edu.my/id/eprint/78047/1/78047.pdf
http://psasir.upm.edu.my/id/eprint/78047/
https://www.mdpi.com/1420-3049/18/12/14711
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spelling my.upm.eprints.780472020-05-03T22:30:49Z http://psasir.upm.edu.my/id/eprint/78047/ Design and synthesis of arylthiophene-2-carbaldehydes via Suzuki-Miyaura reactions and their biological evaluation Ali, Shaukat Rasool, Nasir Ullah, Aman Nasim, Faiz-ul-Hassan Yaqoob, Asma Zubair, Muhammad Rashid, Umer Riaz, Muhammad A series of various novel 4-arylthiophene-2-carbaldehyde compounds were synthesized in moderate to excellent yields via Suzuki-Miyaura cross-coupling with different arylboronic pinacol esters/acids. The synthesized products were screened for their antibacterial, haemolytic, antiurease, and nitric oxide (NO) scavenging capabilities and interestingly, almost all products turned out to have good activities. 3-(5-Formyl-thiophene-3-yl)-5-(trifloromethyl)benzonitrile (2d) revealed excellent antibacterial activity, showing an IC50 value of 29.7 µg/mL against Pseudomonas aeruginosa, compared to the standard drug streptomycin with an IC50 value 35.2 µg/mL and was also found to be the best NO scavenger, with an IC50 value of 45.6 µg/mL. Moreover, 4-(3-chloro-4-fluoro-phenyl)thiophene-2-carbaldehyde (2i) exhibited a superior haemolytic action and an outstanding urease inhibition, showing an IC50 value of 27.1 µg/mL. MDPI 2013 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/78047/1/78047.pdf Ali, Shaukat and Rasool, Nasir and Ullah, Aman and Nasim, Faiz-ul-Hassan and Yaqoob, Asma and Zubair, Muhammad and Rashid, Umer and Riaz, Muhammad (2013) Design and synthesis of arylthiophene-2-carbaldehydes via Suzuki-Miyaura reactions and their biological evaluation. Molecules, 18 (12). pp. 14711-14725. ISSN 1420-3049 https://www.mdpi.com/1420-3049/18/12/14711 10.3390/molecules181214711
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 A series of various novel 4-arylthiophene-2-carbaldehyde compounds were synthesized in moderate to excellent yields via Suzuki-Miyaura cross-coupling with different arylboronic pinacol esters/acids. The synthesized products were screened for their antibacterial, haemolytic, antiurease, and nitric oxide (NO) scavenging capabilities and interestingly, almost all products turned out to have good activities. 3-(5-Formyl-thiophene-3-yl)-5-(trifloromethyl)benzonitrile (2d) revealed excellent antibacterial activity, showing an IC50 value of 29.7 µg/mL against Pseudomonas aeruginosa, compared to the standard drug streptomycin with an IC50 value 35.2 µg/mL and was also found to be the best NO scavenger, with an IC50 value of 45.6 µg/mL. Moreover, 4-(3-chloro-4-fluoro-phenyl)thiophene-2-carbaldehyde (2i) exhibited a superior haemolytic action and an outstanding urease inhibition, showing an IC50 value of 27.1 µg/mL.
format Article
author Ali, Shaukat
Rasool, Nasir
Ullah, Aman
Nasim, Faiz-ul-Hassan
Yaqoob, Asma
Zubair, Muhammad
Rashid, Umer
Riaz, Muhammad
spellingShingle Ali, Shaukat
Rasool, Nasir
Ullah, Aman
Nasim, Faiz-ul-Hassan
Yaqoob, Asma
Zubair, Muhammad
Rashid, Umer
Riaz, Muhammad
Design and synthesis of arylthiophene-2-carbaldehydes via Suzuki-Miyaura reactions and their biological evaluation
author_facet Ali, Shaukat
Rasool, Nasir
Ullah, Aman
Nasim, Faiz-ul-Hassan
Yaqoob, Asma
Zubair, Muhammad
Rashid, Umer
Riaz, Muhammad
author_sort Ali, Shaukat
title Design and synthesis of arylthiophene-2-carbaldehydes via Suzuki-Miyaura reactions and their biological evaluation
title_short Design and synthesis of arylthiophene-2-carbaldehydes via Suzuki-Miyaura reactions and their biological evaluation
title_full Design and synthesis of arylthiophene-2-carbaldehydes via Suzuki-Miyaura reactions and their biological evaluation
title_fullStr Design and synthesis of arylthiophene-2-carbaldehydes via Suzuki-Miyaura reactions and their biological evaluation
title_full_unstemmed Design and synthesis of arylthiophene-2-carbaldehydes via Suzuki-Miyaura reactions and their biological evaluation
title_sort design and synthesis of arylthiophene-2-carbaldehydes via suzuki-miyaura reactions and their biological evaluation
publisher MDPI
publishDate 2013
url http://psasir.upm.edu.my/id/eprint/78047/1/78047.pdf
http://psasir.upm.edu.my/id/eprint/78047/
https://www.mdpi.com/1420-3049/18/12/14711
_version_ 1665896053586526208
score 13.211869

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