Synthesis, characterization and pharmacologically active sulfamethoxazole polymers

Three anti-microbial pharmaceutical drugs were synthesized from two different synthetic routes. 4-acrylamido-N-(5-methyl-3-isoxazolyl)benzenesulfonamide (AMBS) and 4-methacrylamido-N-(5-methyl-3-isoxazolyl)benzenesulfonamide (MMBS) were prepared by reacting acryloyl chloride and methacryloyl chloride with 4-amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide in the presence of triethylamine. N-[4-sulfamido-N-(5-methyl-3-isoxazolyl)phenyl]maleimide (SMPM) was prepared by reacting maleic anhydride with 4-amino-N-(5-methyl-3-isoxazolyl)benzenesulfanamide. These monomers (AMBS, MMBS and SMPM) were polymerized using BPO as a free radical initiator. The pharmacological activity of SMPM compound depends on the functional group in the structure and small structural changes has resulted in higher pharmacological activity of sulfamethoxazole. Thus, maleimide polymer drug conjugate showed greater anti-microbial activity when compared with that of the native drug. (C) 2002 Elsevier Science Ltd. All rights reserved.