We compared the rate of colonic bacterial reduction of disulfide and nitro bonds to that of an azo counterpart. The disulfide and nitro reduction rates are comparable to that of azo having a similar molecular structure. We further explored QSAR of bacterial reduction of different nitro compounds giving a Hammett correlation with ρ=0.553, R2=0.97. We conclude that disulfide and nitro compounds have an unexploited potential for use in prodrugs and drug delivery systems targeted to the colon.