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Int J Mol Sci. 2014 Jan 17;15(1):1237-54. doi: 10.3390/ijms15011237.

Synthesis and antimicrobial evaluation of some novel thiazole, pyridone, pyrazole, chromene, hydrazone derivatives bearing a biologically active sulfonamide moiety.

Author information

1
Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt. elham_darwish@yahoo.com.
2
Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt. azza682000@yahoo.com.
3
Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt. fattaby@hotmail.com.
4
Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt. org.chemo@yahoo.com.

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 13a-e. 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.

PMID:
24445259
PMCID:
PMC3907866
DOI:
10.3390/ijms15011237
[Indexed for MEDLINE]
Free PMC Article

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