Pyrazole and Nicotinonitrile Derivatives Synthesized from Sulfa Drugs, and Their Antibacterial Activity

Utility of sulfadiazine and sulfaguanidine in synthesis of new series of pyrazoles and 2-pyridones is described. Diazotization of sulfadiazine that results in formation of diazonium salt 2 followed by coupling of the latter with active methylene compounds leads to hydrazinyl derivatives 3a–3d . Hete...

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Bibliographic Details
Published in:Russian journal of general chemistry 2019-02, Vol.89 (2), p.339-347
Main Authors: El-Sayed, H. A., Moustafa, A. H., Fadda, A. A., Abd El-Rahman, K. E.
Format: Article
Language:English
Subjects:
Amoxicillin
Catalysis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Coupling (molecular)
Derivatives
Diazo compounds
Hydrazines
Piperidine
Pyrazole
Sulfadiazine
Synthesis
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Summary:Utility of sulfadiazine and sulfaguanidine in synthesis of new series of pyrazoles and 2-pyridones is described. Diazotization of sulfadiazine that results in formation of diazonium salt 2 followed by coupling of the latter with active methylene compounds leads to hydrazinyl derivatives 3a–3d . Heterocyclization of compounds 3a–3c with hydrazine derivatives gives to a series of pyrazole derivatives 4–6 . Similarly, a series of pyrazole derivatives 12–14 is developed from sulfaguanidine. Condensation of hydrazinyl derivatives 3a–3c with cyanoacetamide in the presence of a catalytic amount of piperidine gives 2-oxonicotinonitriles 15a–15c . Tests of the new synthesized compounds against four pathogenic gram (+ve) and gram (−ve) bacteria demonstrate their activity higher than that of the standard Amoxicillin.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363219020270