A series of pyridines and pyridine based sulfa-drugs as antimicrobial agents: Design, synthesis and antimicrobial activity
- Authors: El-Sayed H.A.1, Moustafa A.H.1, El-Torky A.E.1, Abd El-Salam E.A.2
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Affiliations:
- Department of Chemistry, Faculty of Science
- Laboratory of Food Research
- Issue: Vol 87, No 10 (2017)
- Pages: 2401-2408
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/221456
- DOI: https://doi.org/10.1134/S107036321710022X
- ID: 221456
Cite item
Abstract
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.
About the authors
H. A. El-Sayed
Department of Chemistry, Faculty of Science
Author for correspondence.
Email: hasanneg@gmail.com
Egypt, Zagazig
A. H. Moustafa
Department of Chemistry, Faculty of Science
Author for correspondence.
Email: ah_hu_mostafa@yahoo.com
Egypt, Zagazig
A. E. El-Torky
Department of Chemistry, Faculty of Science
Email: ah_hu_mostafa@yahoo.com
Egypt, Zagazig
E. A. Abd El-Salam
Laboratory of Food Research
Email: ah_hu_mostafa@yahoo.com
Egypt, Sharkia