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Int. J. Mol. Sci. 2014, 15(1), 1237-1254; doi:10.3390/ijms15011237
Article

Synthesis and Antimicrobial Evaluation of Some Novel Thiazole, Pyridone, Pyrazole, Chromene, Hydrazone Derivatives Bearing a Biologically Active Sulfonamide Moiety

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Received: 10 November 2013; in revised form: 10 January 2014 / Accepted: 13 January 2014 / Published: 17 January 2014
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Abstract: This study aimed for the synthesis of new heterocyclic compounds incorporating sulfamoyl moiety suitable for use as antimicrobial agents via a versatile, readily accessible N-[4-(aminosulfonyl)phenyl]-2-cyanoacetamide (3). The 2-pyridone derivatives were obtained via reaction of cyanoacetamide with acetylacetone or arylidenes malononitrile. Cycloaddition reaction of cyanoacetamide with salicyaldehyde furnished chromene derivatives. Diazotization of 3 with the desired diazonium chloride gave the hydrazone derivatives 13ae. Also, the reactivity of the hydrazone towards hydrazine hydrate to give Pyrazole derivatives was studied. In addition, treatment of 3 with elemental sulfur and phenyl isothiocyanate or malononitrile furnished thiazole and thiophene derivatives respectively. Reaction of 3 with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt 17 which reacted in situ with 3-(2-bromoacetyl)-2H-chromen-2-one and methyl iodide afforded the thiazole and ketene N,S-acetal derivatives respectively. Finally, reaction of 3 with carbon disulfide and 1,3-dibromopropane afforded the N-[4-(aminosulfonyl) phenyl]-2-cyano-2-(1,3-dithian-2-ylidene)acetamide product 22. All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis. The compounds were evaluated for both their in vitro antibacterial and antifungal activities and showed promising results.
Keywords: sulfamoyl; acrylamide; Pyrazole; pyridones; thiophene; thiazole; antimicrobial activity sulfamoyl; acrylamide; Pyrazole; pyridones; thiophene; thiazole; antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Darwish, E.S.; Fattah, A.M.A.; Attaby, F.A.; Al-Shayea, O.N. Synthesis and Antimicrobial Evaluation of Some Novel Thiazole, Pyridone, Pyrazole, Chromene, Hydrazone Derivatives Bearing a Biologically Active Sulfonamide Moiety. Int. J. Mol. Sci. 2014, 15, 1237-1254.

AMA Style

Darwish ES, Fattah AMA, Attaby FA, Al-Shayea ON. Synthesis and Antimicrobial Evaluation of Some Novel Thiazole, Pyridone, Pyrazole, Chromene, Hydrazone Derivatives Bearing a Biologically Active Sulfonamide Moiety. International Journal of Molecular Sciences. 2014; 15(1):1237-1254.

Chicago/Turabian Style

Darwish, Elham S.; Fattah, Azza M.A.; Attaby, Fawzy A.; Al-Shayea, Oqba N. 2014. "Synthesis and Antimicrobial Evaluation of Some Novel Thiazole, Pyridone, Pyrazole, Chromene, Hydrazone Derivatives Bearing a Biologically Active Sulfonamide Moiety." Int. J. Mol. Sci. 15, no. 1: 1237-1254.



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