Derivatives of 6-aryl-[5-methyl-1-(4-methoxy phenyl)-1,2,3-triazol-4-yl-s-triazolo[3,4-b]-1,3,4-Thiadiazoles (9) and (10) were synthesized by treating p-anisidine with sodium nitrite followed by the addition of sodium azide. Treating azide compound (3) with ethylacetoacetate yielded 1,2,3triazolo-4-carboxylic acid (4), which was converted to ester (5) using absolute ethanol. Treating the ester with hydrazine hydrate afforded the acid hydrazide derivative (6), which was reacted with CS 2 and KOH to produce the salt potassium dithiocarbazate (7). Addition of hydrazine to the salt produced 1-amino-2-mercapto-5-[5-methyl-1-(4-methoxy phenyl)-1,2,3-triazol-4-yl]-1,3,4-triazole (8). Treating (8) with p-chlorobenzoic acid and anisic acid afforded the target compounds (9) and (10).
A new compounds of 2-mercapto-5-phenyl-4,6-dione-1,3,5-tiazino [6,5-b][1,3,4] thiadiazole (2), 2-[2-p-methoxyphenyl-4-oxo-1,3-thiazolidin-3-yl]-5-mercapto-1,3,4-thiadiazole (4), 1-[2-(2-amino-1,3,4-thiadiazol-5-ylthio)acetyl] -2,4,5-trihydropyridazin-3,6-dione (7) and 1-[2-(2-amino-1,3,4-thiadiazole-5-ylthio) acetyl]-3-methylpyrazol-5-one (8) were synthesized in good yield via condensation of 2-amino-5-mercapto-1,3,4-thiadiazole (1) with different organic reagents. All new compounds were tested against three strains of Gram negative bacteria (Escherichia coli, Klebsiella pneumoniae and Proteus vulgaris) and two strains of fungi (Candida albicans and Aspergillus niger), comparing these activities with that of the starting material. Compounds (2), (4), and (7) were highly active against all bacteria strains. Compound (1) was highly active against Candida albicans than others while none of the tested compounds were active against Aspergillus niger.
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