Synthesis and Antifungal Activity of Some Azetidinones

Ethyl-1H-benzotriazol-1-acetate 2 was prepared by reacting 1H-benzotriazole 1 in alcohol with ethyl bromoacetate in presence of anhydrous potassium carbonate, which was treated with hydrazine hydrate under reflux for 1824 hours to obtain the intermediate 1H-benzotriazole-1-acetic acid hydrazide 3. This compound on Schiff’s reaction with aromatic aldehydes in presence of solvent mixture yielded 2-(1H-benzotriazol-1-yl)-N'-(substituted phenyl/heteroaryl methylidene) acetohydrazide 4a-4j. This on reaction with monochloroacetyl chloride and triethylamine in dioxane at low temperature followed by heating at more than 100C temperature gave N-substituted--2-azetidinones 5a-5j and were characterized. .The synthesized compounds exhibited moderate to good antifungal activity when tested in vitro against C.albicans. Compounds 5g and 5h were found to be the most active among all the compounds. To understand their interaction with receptor, these were docked into active site of CYT P-450(PDB-code:1EA1).