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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


Citation

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

Abstract / Synopsis

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.


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Additional Metadata

Item Type: Article
Divisions: Faculty of Biotechnology and Biomolecular Sciences
DOI Number: https://doi.org/10.3390/molecules22020190
Publisher: MDPI
Keywords: Suzuki cross-coupling reaction; Pyridine derivatives; Density functional theory (DFT); Anti-thrombolytic; Biofilm inhibition; Haemolysis
Depositing User: Nurul Ainie Mokhtar
Date Deposited: 09 Nov 2018 16:50
Last Modified: 09 Nov 2018 16:50
Altmetrics: http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.3390/molecules22020190
URI: http://psasir.upm.edu.my/id/eprint/61686
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