Acta Pharm. 63 (2013) 409-418
A convenient synthesis of new NSAID esters containing amino acid, urea and amide moieties
IVANA PERKOVIĆ, ZRINKA RAJIĆ DŽOLIĆ and BRANKA ZORC
University of Zagreb, Faculty of Pharmacy and Biochemistry, Zagreb, Croatia
Accepted March 12, 2013
A convenient synthetic method for the preparation of novel NSAID twin esters 6a-i containing amino acid residue, urea and amide moieties has been developed. The synthetic pathway applied for the preparation of target compounds and key intermediates 1-benzotriazolecarboxylic acid chloride (1), NSAID benzotriazolides 2a-c and N-(1-benzotriazolecarbonyl)-amino acids 3a-d involved benzotriazole as a synthetic auxiliary. The final preparation step of esters 6a-i included the solvent-free reaction of compounds 2a-c with amino acid derivatives 5a-g, bearing two hydroxyl groups, one at each terminal, beside urea and amide functionalities.
Keywords: NSAID, ester, amino acid, benzotriazole, urea, amide