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.
abstract: The present study describes palladium-catalyzed one pot Suzuki cross-coupling reaction to synthesize a series of novel pyridine derivatives2a-2i,4a-4i. In brief, Suzuki cross-coupling reaction of 5-bromo-2-methylpyridin-3-amine (1) directly or viaN-[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 derivatives2a-2iand4a-4iby 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 compound4bexhibited the highest percentage lysis value (41.32%) against clot formation in human blood among all newly synthesized compounds. In addition, the compound4fwas found to be the most potent againstEscherichia coliwith an inhibition value of 91.95%. The rest of the pyridine derivatives displayed moderate biological activities.
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. Gulchemist35@gmail.com.
authors.forename: Gulraiz
authors.initials: G
authors.lastname: Ahmad
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. nasirrasool@gcuf.edu.pk.
authors.forename: Nasir
authors.initials: N
authors.lastname: Rasool
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. chemistue@gmail.com.
authors.forename: Hafiz Mansoor
authors.initials: HM
authors.lastname: Ikram
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. samreengul@gcuf.edu.pk.
authors.forename: Samreen
authors.initials: S
authors.lastname: Gul Khan
authors.affiliation: Department of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, 22060 Abbottabad, Pakistan. mahmood@ciit.net.pk.
authors.forename: Tariq
authors.initials: T
authors.lastname: Mahmood
authors.affiliation: Department of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, 22060 Abbottabad, Pakistan. khurshid@ciit.net.pk.
authors.forename: Khurshid
authors.initials: K
authors.lastname: Ayub
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. nr_308@hotmail.com.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Zubair
authors.affiliation: Chemistry Department, Faculty of Science, Taif University, 888-Taif, Saudi Arabia. em-s_z@yahoo.com.
authors.forename: Eman
authors.initials: E
authors.lastname: Al-Zahrani
authors.affiliation: Sustainable Energy Technologies Center, College of Engineering, P.O. Box 800, King Saud University, Riyadh 11421, Saudi Arabia. ranausmanali4u@gmail.com.
authors.forename: Usman
authors.initials: U
authors.lastname: Ali Rana
authors.affiliation: Faculty of Industrial Sciences & Technology, University Malaysia Pahang, Lebuhraya Tun, Razak 26300, Kuantan Pahang, Malaysia. nadeemupm@gmail.com.
authors.forename: Muhammad Nadeem
authors.initials: MN
authors.lastname: Akhtar
authors.affiliation: Faculty of Biotechnology and Biomolecular Sciences, University Putra Malaysia, Serdang, Selangor Darul Ehsan 43400, Malaysia. noorjahan@upm.edu.my.
authors.forename: Noorjahan Banu
authors.initials: NB
authors.lastname: Alitheen
mesh_terms: D000588:Amines / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology; D018441:Biofilms / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D005343:Fibrinolytic Agents / Q000737:chemistry / Q000494:pharmacology; D006461:Hemolysis / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000588:Amines; D000890:Anti-Infective Agents; D005343:Fibrinolytic Agents; D011725:Pyridines
keywords: Suzuki cross-coupling reaction; anti-thrombolytic; biofilm inhibition; density functional theory (DFT); haemolysis; pyridine derivatives