Synthesis, antimicrobial activity and conformational analysis of novel substituted pyridines: BF(3)-promoted reaction of hydrazine with 2-alkoxy pyridines.
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.
Goda
Fatma E
FE
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt. fatma_goda@yahoo.com
Abdel-Aziz
Alaa A-M
AA
Attef
Omer A
OA
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
D000890:Anti-Infective Agents; D006834:Hydrazines; D011725:Pyridines; C029424:hydrazine