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

Bibliographic Details
Main Authors:	Gulraiz, Ahmad, Rasool, Nasir, Ikram, Hafiz Mansoor, Khan, Samreen Gul, Mahmood, Tariq, Ayub, Khurshid, Zubair, Muhammad, Al-Zahrani, Eman, Rana, Usman Ali, Akhtar, Muhammad Nadeem, Noorjahan Banu, Alitheen
Format:	Article
Language:	English
Published:	MDPI - Open Access Publishing 2017
Subjects:	Q Science (General)
Online Access:	http://umpir.ump.edu.my/id/eprint/19768/ http://umpir.ump.edu.my/id/eprint/19768/ http://umpir.ump.edu.my/id/eprint/19768/ http://umpir.ump.edu.my/id/eprint/19768/1/fist-2017-nadeem-Efficient%20Synthesis%20of%20Novel%20Pyridine-Based.pdf

id	ump-19768
recordtype	eprints
spelling	ump-197682017-12-29T05:23:12Z http://umpir.ump.edu.my/id/eprint/19768/ 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 Gulraiz, Ahmad Rasool, Nasir Ikram, Hafiz Mansoor Khan, Samreen Gul Mahmood, Tariq Ayub, Khurshid Zubair, Muhammad Al-Zahrani, Eman Rana, Usman Ali Akhtar, Muhammad Nadeem Noorjahan Banu, Alitheen Q Science (General) 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 - Open Access Publishing 2017 Article PeerReviewed application/pdf en cc_by http://umpir.ump.edu.my/id/eprint/19768/1/fist-2017-nadeem-Efficient%20Synthesis%20of%20Novel%20Pyridine-Based.pdf Gulraiz, Ahmad 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 Noorjahan Banu, Alitheen (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 (print); 1420-3049 (online) http://dx.doi.org/10.3390/molecules22020190 doi: 10.3390/molecules22020190
repository_type	Digital Repository
institution_category	Local University
institution	Universiti Malaysia Pahang
building	UMP Institutional Repository
collection	Online Access
language	English
topic	Q Science (General)
spellingShingle	Q Science (General) Gulraiz, Ahmad Rasool, Nasir Ikram, Hafiz Mansoor Khan, Samreen Gul Mahmood, Tariq Ayub, Khurshid Zubair, Muhammad Al-Zahrani, Eman Rana, Usman Ali Akhtar, Muhammad Nadeem Noorjahan Banu, Alitheen 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
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	Gulraiz, Ahmad Rasool, Nasir Ikram, Hafiz Mansoor Khan, Samreen Gul Mahmood, Tariq Ayub, Khurshid Zubair, Muhammad Al-Zahrani, Eman Rana, Usman Ali Akhtar, Muhammad Nadeem Noorjahan Banu, Alitheen
author_facet	Gulraiz, Ahmad Rasool, Nasir Ikram, Hafiz Mansoor Khan, Samreen Gul Mahmood, Tariq Ayub, Khurshid Zubair, Muhammad Al-Zahrani, Eman Rana, Usman Ali Akhtar, Muhammad Nadeem Noorjahan Banu, Alitheen
author_sort	Gulraiz, Ahmad
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 - Open Access Publishing
publishDate	2017
url	http://umpir.ump.edu.my/id/eprint/19768/ http://umpir.ump.edu.my/id/eprint/19768/ http://umpir.ump.edu.my/id/eprint/19768/ http://umpir.ump.edu.my/id/eprint/19768/1/fist-2017-nadeem-Efficient%20Synthesis%20of%20Novel%20Pyridine-Based.pdf
first_indexed	2023-09-18T22:28:20Z
last_indexed	2023-09-18T22:28:20Z
_version_	1777416117507063808

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

Similar Items