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Sulfamethazine (SMZ) ( 1 ) is an antibacterial  sulfa drug  which suppresses the synthesis of dihydrofolic acid. It is used for the treatment of infections in livestock; such as gastrointestinal, and respiratory tract infections. During the current study, synthesis, characterization, and evaluation of immunomodulatory activities of derivatives of sulfamethazine (SMZ) ( 3–39 ) was carried out. These derivatives were synthesized by the reaction of sulfamethazine with a range of acid chlorides. All the compounds were characterized by using modern spectroscopic techniques, such as  1 H-, and  13 C-NMR, EI-MS, and HRFAB-MS. Compounds  3–10 ,  14 , and  15  were identified as new compounds. Immunomodulatory effect of compounds  3–39  on different parameters of innate immune response was evaluated, including the production of Reactive Oxygen Species (ROS) from human whole blood and isolated polymorphonuclear neutrophils (PMNs), nitric oxide (NO), and pro-inflammatory cytokine TNF-α. All the new compounds, except  14  and  15 , showed a significant anti-inflammatory activity. Compounds  3–39  were also evaluated for their anti-bacterial activity and cytotoxicity (3T3 mouse fibroblast cell lines). All the compounds were found to be non-cytotoxic against normal cell lines.

Sulphamethazine derivatives as immunomodulating agents: New therapeutic strategies for inflammatory diseases