28793-03-5

Currently available chemotherapeutic drugs against hematological malignancies have several adverse effects and are associated with high mortality rates. Thus, in this study we evaluated the cytotoxic effect of 26 new sulfonamide derivatives on acute leuke

The Friedel-Crafts reaction of 1-benzenesulfonyl-2-(bromomethyl)ethylenimine-2-(14)C and benzene yields 3,3-diphenyl-1-benzenesulfonamidopropane-2-(14)C.This finding, coupled with the results of an earlier tracer study, shows that the order of atoms in the three-carbon chain of the starting etylenimine persists unchanged in the product.If so, a previously suggested pathway becomes unacceptable.Of the several test compounds exposed to the action of aluminum chloride and benzene as described in the present work, only 1-benzenesulfonyl-2-benzylethylenimine and 1-benzenesulfonyl-2-phenylazetidine gave 3,3-diphenyl-1-benzenesulfonamidopropane.Since the azetidine compound could be eliminated as an intermediate in the ethylenimine process, this left only the benzyl derivative as an eligible intermediate.These data led to a revised pathway, which accommodates all the facts.An early stage in the mechanism is taken as conversion of the ethylenimine starting material to 1-benzenesulfonyl-2-benzylethylenimine.Under the reaction conditions, the latter compound generates a carbocationoid center on the middle carbon atom of its three-carbon chain.By a 1,2 hydride shift, this carbocation rearranges to the more stable benzylic carbocation, which combines with benzene to form the final product.