Journal
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
Volume 87, Issue 10, Pages 2401-2408Publisher
MAIK NAUKA/INTERPERIODICA/SPRINGER
DOI: 10.1134/S107036321710022X
Keywords
substituted pyridine; sulfa-drug; tetrazolo[1,5-a]pyridine; antimicrobial activity
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Herein, we report a series of pyridines and their sulfa drug derivatives as antimicrobial agents. Regioselective alkylation followed by hydrozinolysis of 2-pyridone 1 gave the target compounds 2 and 3. Compound 3 was cyclized with acetylacetone or heated in dry benzene to give 2-(pyrazol-1-yl)nicotinonitrile 5 and 3-amino-1H-pyrazolo[3,4-b]pyridine derivatives 6, respectively. Diazotization of compound 3 with nitrous acid at low temperature afforded tetrazolo[1,5-a]pyridine derivative 8. Compounds 6 and 7 were obtained by condensation of hydrazine derivative 3 with D-glucose and D-ribose. Acid-mediated hydrolysis and sulfurization of dicyano compound 2 gave pyridine-3,5-dicarboxamide 11 and 2-thioxopyridine 12 derivatives, respectively. The later compound was alkylated with allyl bromide, benzyl chloride and mono chloroacetic acid to produce the corresponding S-alkylated derivatives 13-15. Compound 15 underwent the Thrope-Ziegler cyclization/condensation with sulfa-drugs to give the corresponding thienopyridine 16 and sulfonamide derivatives 17-19. Antimicrobial study of the new syntheized compounds demonstrated signficant activity of compounds 8-11 and 17-19.
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