DEVELOPMENT AND OPTIMIZATION OF THE SYNTHESIS OF NEW THIAZOLIDIN-4-ONE DERIVATIVES OF IBUPROFEN

Ibuprofen, an important nonsteroidal anti-inflammatory agent, is one of the most prescribed drugs for the treatment of pain and inflammation from various rheumatic diseases, but some side effects can occur on long-term use. Aim: The method for synthesis optimization of derivatives of Ibuprofen with thiazolidin-4-one moiety, with improved pharmacological and toxicological profile. Material and methods: To optimize the derivatization method of free carboxyl group of Ibuprofen (2( 4-isobutylphenyl) propionic acid) the reaction conditions were varied (reagent ratio, catalyst, reaction medium). Results: The most favorable method was proved to be the reaction between ibuprofen hydrazone and mercaptoacetic acid, in excess, at 80-85 degrees C, for 6 h with 96% conversion rate. Conclusions: The synthesis of 2-phenyl-3-[2-(4-(isobutyl)phenyl)-2methyl] acetamido-thiazolidin-4-one derivative was optimized in view of applying it as a general procedure for the synthesis of other derivatives with related structure. The chemical structure and molecular weight of the synthesized compound were confirmed by spectral methods (IR, H-1 NMR, C-13 NMR, HR-MS).