Investigation on the cytotoxic effects of nitrogen-mustard-derived Schiff bases. Studies on the reactivity of the N-mustard pharmacophoric group

4-[bis(2-chloroethyl)amino]benzaldehyde-N(4)-phenyl-thiosemicarbazone (1), 4-[bis(2-chloroethyl)amino]benzaldehyde-N(4)-para-chloro-phenyl-thiosemicarbazone (2), 4-[bis(2-chloroethyl)amino]benzaldehyde-N(4)-methyl-thiosemicarbazone (3) and 4-[bis(2-chloroethyl)amino]benzaldehyde-benzoylhydrazone (4) were obtained by functionalization of the bis(2-chloroethyl)amino DNA alkylating group with a thiosemicarbazone/hydrazone moiety. The compounds were fully characterized by means of their infrared (including theoretical vibrational analyses) and NMR spectra, as well as by means of X-ray crystal structure determinations.