SYNTHESIS AND STUDY OF NEW N-SUBSTITUTED CARBAZOLE AS SOME ANTIFUNGAL AGENTS

Abstract

Carbazole (1) upon condensation with ethylchloroacetate followed by treatment with hydrazine hydrate yielded 2-(9H-carbazol-9-yl) acetohydrazide (3). Treatment of compound (3) with sodium nitrite resulted in the formation of diazonium salt (4). Reaction of (4) with ethylacetoacetate and acetylacetone afforded ethyl 2-[3-(9H-carbazol-9-ylacetyl) triazanylidene]-3-oxobutanoate (5) and 3-[3-(9H-carbazol-9-ylacetyl)triazanylidene] pentane-2,4-dione (6), respectively. Reaction of (5) and (6) with phenylhydrazine and urea yielded 4-[3-(9H-carbazol-9-ylacetyl)triazanylidene]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (7) and 5-[3-(9H-carbazol-9-ylacetyl) triazanylidene]-4,6-dimethylpyrimidin-2(5H)-one (8), respectively. The newly synthesized compounds were characterized by IR, 1H-NMR and 13C-NMR analysis. Potential antifungal effects of the synthesized compounds were investigated using the Candida albicans and Aspergillus niger strains. The newly synthesized compounds exhibited promising activities, particularly compounds (7, 8 and 9).