Here, we synthesized and studied a library of 2,4-dinitrophenylsulfonamides that closely resembled N-benzyl-2,4-dinitrophenylsulfonamide (1), a thiol-activated prodrug of sulfur dioxide (SO 2 ) which has shown high potency as a Mycobacterium tuberculosis (Mtb) inhibitory agent. The ability of these compounds to generate SO 2 in the presence of a thiol was evaluated. A good correlation between pK aH of the corresponding amine and reactivity with thiols to generate SO 2 was found suggesting that the rate determining step of SO 2 generation involved protonation of the amine. Amongst analogues with measurable MICs, we also found a correlation between ability to generate SO 2 and Mtb growth inhibitory activity. Together, we report several thiol-mediated prodrugs of SO 2 which strongly inhibited Mtb growth (MIC <1μgmL −1 ) with potential for further development as tuberculosis drug candidates.