303755-57-9

Upstream product

• 1656-44-6 2,4-dinitrobenzenesulfonyl chloride 
• 90-04-0 2-methoxy-phenylamine 

Downstream Products

• 23815-63-6 1-(S-cysteil) 2,4-dinitrobenzene 
• 3165-76-2 S-(2,4-Dinitrophenyl)-cystein 
• 50798-94-2 N-benzyl-2-methoxyaniline 
• 7446-09-5 sulfur dioxide 
• 90-04-0 2-methoxy-phenylamine 
• 10541-78-3 2-methoxy-N-methylaniline 
• 15258-47-6 2-methoxy-N-allylaniline 
• 65570-20-9 butyl-(2-methoxy-phenyl)amine 
• 139944-56-2 N-propyl-2-methoxyaniline 
• 15258-43-2 N-ethyl-2-methoxyaniline 
• 1606142-72-6 N-benzyl-N-(3-(N-(2-methoxyphenyl)-2,4-dinitrophenylsulfonamido)propyl)-2,4-dinitrobenzenesulfonamide 

Relevant academic research and scientific papers

THIOL MEDIATED/ACTIVATED PRODRUGS OF SULFUR DIOXIDE (SO2) HAVING ANTI-BACTERIAL ACTIVITY

Disclosed herein are thiol mediated/activated prodrugs of SO2, particularly 2,4-dinitrophenylsulfonamide analogues, having Formula-I or pharmaceutically acceptable salts thereof exhibiting tunable release profiles of SO2 with significant therapeutic efficacy against bacterial infections. Further, the present invention provides pharmaceutical compositions comprising compound of Formula I or pharmaceutically acceptable salts thereof, along with pharmaceutically acceptable carriers/excipients.

Synthesis and antimycobacterial activity of prodrugs of sulfur dioxide (SO2)

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 (SO2) which has shown high potency as a Mycobacterium tuberculosis (Mtb) inhibitory agent. The ability of these compounds to generate SO2 in the presence of a thiol was evaluated. A good correlation between pKaH of the corresponding amine and reactivity with thiols to generate SO2 was found suggesting that the rate determining step of SO2 generation involved protonation of the amine. Amongst analogues with measurable MICs, we also found a correlation between ability to generate SO2 and Mtb growth inhibitory activity. Together, we report several thiol-mediated prodrugs of SO2 which strongly inhibited Mtb growth (MIC -1) with potential for further development as tuberculosis drug candidates.