Schiff bases of methanesulfonylhydrazine. Synthesis, spectroscopic characterization, conformational analysis, and biological activity

Three novel Schiff bases: salicylaldehyde methanesulfonylhydrazone (1), 2-h ydroxyacetophenone methanesulfonylhydrazone (2) and 2-hydroxy-1-naphthaldeh yde methanesulfonylhydrazone (3) have been synthesized. Compounds 1-3, as w ell as acetone methanesulfonylhydrazone (4) have been characterized by TLC, H-1 NMR and IR spectra. The spectroscopic results for 1-3 have revealed th e presence of an intramolecular hydrogen bond between the hydroxyl group an d the imine N atom. The conformational isomerism of 1-4 with respect to the rotations around the SN and NN bonds have been studied by the method of mo lecular mechanics. Compounds 1-4 and methanesulfonylhydrazine exhibit antib acterial and cytotoxic effects.