P. Sah, Pratibha Bidawat, M. Seth
Apr 1, 2014
Citations
0
Influential Citations
27
Citations
Journal
Arabian Journal of Chemistry
Abstract
Abstract 5-(4-Chlorophenyl amino)-2-mercapto-1,3,4-thiadiazole ( I ) was refluxed with formaldehyde and ammonium chloride in ethanol yielding the Mannich base 5-(4-chloro phenyl amino)-3-aminomethyl-2-mercapto-1,3,4-thiadiazole ( II ). Esterification with 4-chloro-(2,6-dinitro phenoxy)-ethyl acetate ( III ) under anhydrous conditions gave the intermediate ( IV ). Subsequent hydrazinolysis with hydrazine hydrate gave the corresponding hydrazide 3-amino methyl-5-(4-chloro phenyl amino)-2-mercapto-4′-(2′,6′-dinitro phenoxy)-acetyl hydrazide ( V ). The hydrazide was converted into the Schiff bases ( VI a – b ) by reacting with 2-chlorobenzaldehyde and 3-methoxy-4-hydroxy benzaldehyde in presence of methanol containing 2–3 drops of acetic acid. Diazotisation with aromatic amines, sulphanilic acid and sulphur drugs gave the formazans ( VII a – g ) respectively. Chemical structures have been established by elemental analysis and the spectral techniques of FTIR, 1 H NMR and mass. Antimicrobial activity ( in vitro ) was evaluated against the two pathogenic bacterial strains. Escherichia coli and Salmonella typhi , three fungal strains Aspergillus niger , Penicillium species and Candida albicans . The compounds have shown moderate activity.