Diversity-oriented synthesis of novel sulfonated piperazine derivatives endowing dual biological activities

A catalyst-free synthetic route for the diversity-oriented synthesis of sulfonated piperazine derivatives containing dithiocarbamates, thiol and azide functional groups was developed via DABCO C-N bond cleavage. In this synthetic strategy, quaternized DABCO salts were synthesized using sultones and reacted with various nucleophiles namely dithiocarbamates, thiols and sodium azide to afford the target functionalized sulfonated piperazines derivatives in moderate to excellent yields. It is the first report on using sultones as activating agents for DABCO bond cleavage. Finally, the ensued products revealed acceptable antibacterial activity as examined by disc fusion and microdilution methods against both Gram-positive and Gram-negative bacteria like S. aureus and E. coli. More importantly, some of the ensured products simultaneously demonstrated anti-glioma effects with a negligible killing effect on mammalian cells.