Lewis acid-promoted transformation of 2-alkoxypyridines into 2-aminopyridines and their antibacterial activity. Part 2: Remarkably facile C–N bond formation

• Published in: Bioorganic & medicinal chemistry Vol. 13; no. 16; pp. 4929 - 4935
• Main Authors: Abdel-Aziz, Alaa A.-M., El-Subbagh, Hussein I., Kunieda, Takehisa
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 15.08.2005; Elsevier Science
• Subjects: 2-Alkoxypyridines; 2-Aminopyridines; Aminopyridines - chemical synthesis; Aminopyridines - pharmacology; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Biological and medical sciences; Escherichia coli - drug effects; Lewis acid; Magnetic Resonance Spectroscopy; Medical sciences; Microbial Sensitivity Tests; Models, Molecular; Molecular Conformation; Molecular modeling; Pharmacology. Drug treatments; Pyridines - chemical synthesis; Pyridines - chemistry; Pyridines - pharmacology; Quantitative Structure-Activity Relationship; Staphylococcus aureus - drug effects; Structure-Activity Relationship; Lewis acid; Antibacterial activity; 2-Aminopyridines; 2-Alkoxypyridines; Molecular modeling; Nitrile; Escherichia coli; NMR spectrometry; Modeling; Pyridine derivatives; Amine; Structure activity relation; Molecular model; Force field method; Bacteria; Micrococcales; Micrococcaceae; Staphylococcus aureus; Enterobacteriaceae; Catalytic reaction; Nucleophilic reaction; Prediction; Acid catalysis; Ketone; In vitro; Antibacterial agent; Nucleophilic substitution
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2005.05.027

[Display omitted] 2-Alkoxy-3-cyano-4,6-diarylpyridines 1a, b which were synthesized by condensation of α,β-unsaturated ketones with malononitrils were subjected to Lewis acid-catalyzed nucleophilic displacement reaction with various amines to afford the corresponding 2-aminopyridines 3– 21. The potency of the results as antibacterial agents has been evaluated. The structure of the newly prepared compounds was assessed by microanalysis, IR, and NMR spectra. Molecular modeling and QSAR methods are used to study the antibacterial activity of the active compounds by means of the molecular mechanic method.