Cover Image

Efficient synthesis of novel pyridine-based derivatives via Suzuki cross-coupling reaction of commercially available 5-bromo-2-methylpyridin-3-amine: quantum mechanical investigations and biological activities

The present study describes palladium-catalyzed one pot Suzuki cross-coupling reaction to synthesize a series of novel pyridine derivatives 2a-2i, 4a-4i. In brief, Suzuki cross-coupling reaction of 5-bromo-2-methylpyridin-3-amine (1) directly or via N-[5-bromo-2-methylpyridine-3-yl]acetamide (3) wit...

Full description

Saved in:
Bibliographic Details
Main Authors: Ahmad, Gulraiz, Rasool, Nasir, Ikram, Hafiz Mansoor, Khan, Samreen Gul, Mahmood, Tariq, Ayub, Khurshid, Zubair, Muhammad, Al-Zahrani, Eman, Rana, Usman Ali, Akhtar, Muhammad Nadeem, Alitheen, Noorjahan Banu
Format: Article
Language:English
Published: MDPI 2017
Online Access:http://psasir.upm.edu.my/id/eprint/61686/1/Efficient%20synthesis%20of%20novel%20pyridine.pdf
http://psasir.upm.edu.my/id/eprint/61686/
https://www.mdpi.com/1420-3049/22/2/190
Tags: Add Tag
No Tags, Be the first to tag this record!
id my.upm.eprints.61686
record_format eprints
spelling my.upm.eprints.616862018-11-09T08:50:13Z http://psasir.upm.edu.my/id/eprint/61686/ Efficient synthesis of novel pyridine-based derivatives via Suzuki cross-coupling reaction of commercially available 5-bromo-2-methylpyridin-3-amine: quantum mechanical investigations and biological activities Ahmad, Gulraiz Rasool, Nasir Ikram, Hafiz Mansoor Khan, Samreen Gul Mahmood, Tariq Ayub, Khurshid Zubair, Muhammad Al-Zahrani, Eman Rana, Usman Ali Akhtar, Muhammad Nadeem Alitheen, Noorjahan Banu The present study describes palladium-catalyzed one pot Suzuki cross-coupling reaction to synthesize a series of novel pyridine derivatives 2a-2i, 4a-4i. In brief, Suzuki cross-coupling reaction of 5-bromo-2-methylpyridin-3-amine (1) directly or via N-[5-bromo-2-methylpyridine-3-yl]acetamide (3) with several arylboronic acids produced these novel pyridine derivatives in moderate to good yield. Density functional theory (DFT) studies were carried out for the pyridine derivatives 2a-2i and 4a-4i by using B3LYP/6-31G(d,p) basis with the help of GAUSSIAN 09 suite programme. The frontier molecular orbitals analysis, reactivity indices, molecular electrostatic potential and dipole measurements with the help of DFT methods, described the possible reaction pathways and potential candidates as chiral dopants for liquid crystals. The anti-thrombolytic, biofilm inhibition and haemolytic activities of pyridine derivatives were also investigated. In particular, the compound 4b exhibited the highest percentage lysis value (41.32%) against clot formation in human blood among all newly synthesized compounds. In addition, the compound 4f was found to be the most potent against Escherichia coli with an inhibition value of 91.95%. The rest of the pyridine derivatives displayed moderate biological activities. MDPI 2017 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/61686/1/Efficient%20synthesis%20of%20novel%20pyridine.pdf Ahmad, Gulraiz and Rasool, Nasir and Ikram, Hafiz Mansoor and Khan, Samreen Gul and Mahmood, Tariq and Ayub, Khurshid and Zubair, Muhammad and Al-Zahrani, Eman and Rana, Usman Ali and Akhtar, Muhammad Nadeem and Alitheen, Noorjahan Banu (2017) Efficient synthesis of novel pyridine-based derivatives via Suzuki cross-coupling reaction of commercially available 5-bromo-2-methylpyridin-3-amine: quantum mechanical investigations and biological activities. Molecules, 22 (2). pp. 1-19. ISSN 1420-3049 https://www.mdpi.com/1420-3049/22/2/190 10.3390/molecules22020190
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 describes palladium-catalyzed one pot Suzuki cross-coupling reaction to synthesize a series of novel pyridine derivatives 2a-2i, 4a-4i. In brief, Suzuki cross-coupling reaction of 5-bromo-2-methylpyridin-3-amine (1) directly or via N-[5-bromo-2-methylpyridine-3-yl]acetamide (3) with several arylboronic acids produced these novel pyridine derivatives in moderate to good yield. Density functional theory (DFT) studies were carried out for the pyridine derivatives 2a-2i and 4a-4i by using B3LYP/6-31G(d,p) basis with the help of GAUSSIAN 09 suite programme. The frontier molecular orbitals analysis, reactivity indices, molecular electrostatic potential and dipole measurements with the help of DFT methods, described the possible reaction pathways and potential candidates as chiral dopants for liquid crystals. The anti-thrombolytic, biofilm inhibition and haemolytic activities of pyridine derivatives were also investigated. In particular, the compound 4b exhibited the highest percentage lysis value (41.32%) against clot formation in human blood among all newly synthesized compounds. In addition, the compound 4f was found to be the most potent against Escherichia coli with an inhibition value of 91.95%. The rest of the pyridine derivatives displayed moderate biological activities.
format Article
author Ahmad, Gulraiz
Rasool, Nasir
Ikram, Hafiz Mansoor
Khan, Samreen Gul
Mahmood, Tariq
Ayub, Khurshid
Zubair, Muhammad
Al-Zahrani, Eman
Rana, Usman Ali
Akhtar, Muhammad Nadeem
Alitheen, Noorjahan Banu
spellingShingle Ahmad, Gulraiz
Rasool, Nasir
Ikram, Hafiz Mansoor
Khan, Samreen Gul
Mahmood, Tariq
Ayub, Khurshid
Zubair, Muhammad
Al-Zahrani, Eman
Rana, Usman Ali
Akhtar, Muhammad Nadeem
Alitheen, Noorjahan Banu
Efficient synthesis of novel pyridine-based derivatives via Suzuki cross-coupling reaction of commercially available 5-bromo-2-methylpyridin-3-amine: quantum mechanical investigations and biological activities
author_facet Ahmad, Gulraiz
Rasool, Nasir
Ikram, Hafiz Mansoor
Khan, Samreen Gul
Mahmood, Tariq
Ayub, Khurshid
Zubair, Muhammad
Al-Zahrani, Eman
Rana, Usman Ali
Akhtar, Muhammad Nadeem
Alitheen, Noorjahan Banu
author_sort Ahmad, Gulraiz
title Efficient synthesis of novel pyridine-based derivatives via Suzuki cross-coupling reaction of commercially available 5-bromo-2-methylpyridin-3-amine: quantum mechanical investigations and biological activities
title_short Efficient synthesis of novel pyridine-based derivatives via Suzuki cross-coupling reaction of commercially available 5-bromo-2-methylpyridin-3-amine: quantum mechanical investigations and biological activities
title_full Efficient synthesis of novel pyridine-based derivatives via Suzuki cross-coupling reaction of commercially available 5-bromo-2-methylpyridin-3-amine: quantum mechanical investigations and biological activities
title_fullStr Efficient synthesis of novel pyridine-based derivatives via Suzuki cross-coupling reaction of commercially available 5-bromo-2-methylpyridin-3-amine: quantum mechanical investigations and biological activities
title_full_unstemmed Efficient synthesis of novel pyridine-based derivatives via Suzuki cross-coupling reaction of commercially available 5-bromo-2-methylpyridin-3-amine: quantum mechanical investigations and biological activities
title_sort efficient synthesis of novel pyridine-based derivatives via suzuki cross-coupling reaction of commercially available 5-bromo-2-methylpyridin-3-amine: quantum mechanical investigations and biological activities
publisher MDPI
publishDate 2017
url http://psasir.upm.edu.my/id/eprint/61686/1/Efficient%20synthesis%20of%20novel%20pyridine.pdf
http://psasir.upm.edu.my/id/eprint/61686/
https://www.mdpi.com/1420-3049/22/2/190
_version_ 1643837573358944256
score 13.211869

Similar Items