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Vol. 27 No. 12 (2015): Vol 27 Issue 12

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Synthesis, in vitro Antimicrobial and Anticancer Evaluation of Some New Pyridazines and Polyfunctionally Substituted Heterocyclic Compounds

https://doi.org/10.14233/ajchem.2015.19123
F.M.A. Altalbawy
Department of Measurements and Environmental Applications, National Institute of Laser Enhanced Sciences, Cairo University, P.O. Box 12613, Giza, Egypt

Corresponding Author(s) : F.M.A. Altalbawy

f_altalbawy@yahoo.com

Asian Journal of Chemistry, Vol. 27 No. 12 (2015): Vol 27 Issue 12

Abstract

This study aimed for the synthesis of new heterocyclic compounds incorporating sulfamoyl moiety suitable for use as antimicrobial agents via versatile and readily accessible N-[4-(aminosulfonyl)phenyl]-3-oxobutanamide (1). Butanamide coupled with arenediazonium salts to afford hydrazones. The latter reacts with dimethylformamide dimethyl acetal (DMF-DMA) to afford the substituted 1,4-dihydropyridazine. Several new thiophene, pyridine, nicotinamide and pyrazole derivatives have been synthesized by the reactions of butanamide with malononitrile and elemental sulfur, 1,3-diphenylpropenone, arylidenecyanothioacetamide, nitrogen nucleophiles, respectively. Refluxing of butanamide with a mixture of p-methoxybenzaldehyde and thiourea afforded 4-(4-methoxyphenyl)-6-methyl-N-(4-sulfamoylphenyl)-2-thioxo-1,2-dihydropyrimidine-5-carboxamide which heated with chloroacetyl chloride give N-[4-(aminosulfonyl)phenyl]-7-methyl-5-(4-methoxyphenyl)-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide. Treatment of butanamide with phenyl isothiocyanate afforded the intermediate salt which reacted in situ with 2-bromo-1-phenylethanone to afford N-[4-(aminosulfonyl)phenyl]-2-(3,4-diphenyl-3H-thiazol-2-ylidene)-3-oxobutanamide. Some of the selected products were evaluated for both their in vitro antibacterial and antifungal activities and showed promising results. In addition, the anticancer activity of some selected products against human liver (HEPG2) cell line was determined and the results revealed high activities of compounds 5a, 6 and 14.

Keywords

Antimicrobial Activity Anticancer Activity Butanamide Pyrazole Pyridine Thiophene Thiazolopyrimidine
Altalbawy, F. (2015). Synthesis, in vitro Antimicrobial and Anticancer Evaluation of Some New Pyridazines and Polyfunctionally Substituted Heterocyclic Compounds. Asian Journal of Chemistry, 27(12), 4361–4368. https://doi.org/10.14233/ajchem.2015.19123
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