title: Synthesis, antimicrobial activity and conformational analysis of novel substituted pyridines: BF(3)-promoted reaction of hydrazine with 2-alkoxy pyridines.
abstract: Some new 2-alkoxy-3-cyano-4,6-diarylpyridines 3,4 were synthesized by condensation of different alpha,beta-unsaturated ketones 1 with malononitrile 2, followed by cyclization in sodium alkoxide/alcohol system. Lewis acid-catalyzed reaction of 4 with hydrazine afforded the corresponding 1H-pyrazolo[3,4-b]pyridines 5. The potency of the results as antimicrobial agents has been evaluated. The structure of the newly prepared compounds was assessed by microanalysis, IR and NMR spectra. Molecular mechanics (MM2) and semiemperical (AM1) molecular orbital calculations have been performed for the most biologically active compounds 5b and c to get insight into their molecular structures and to learn more about their stable molecular conformations.
authors.affiliation: Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt. fatma_goda@yahoo.com
authors.forename: Fatma E
authors.initials: FE
authors.lastname: Goda
authors.forename: Alaa A-M
authors.initials: AA
authors.lastname: Abdel-Aziz
authors.forename: Omer A
authors.initials: OA
authors.lastname: Attef
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006834:Hydrazines / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests / Q000379:methods; D008968:Molecular Conformation; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000890:Anti-Infective Agents; D006834:Hydrazines; D011725:Pyridines; C029424:hydrazine