Synthesis and biological screening of some novel amidocarbamate derivatives of ketoprofen

Abstract: A series of novel ketoprofen derivatives 4a–j bearing both amide and carbamate functionalities were prepared using benzotriazole. Selective reduction of ketoprofen produced hydroxy derivative 2, which reacts with one or 2 mol of 1-benzotriazole carboxylic acid chloride (1) gave benzotriazole derivatives 3a and 3b respectively. Antioxidative screenings revealed that the prepared compounds 3b and 4a–j possess excellent lipid peroxidation inhibition at 0.1 mM concentration. Two of the compounds 3b and 4g also showed high soybean lipoxygenase inhibition activity, where as the amidocarbamate derivatives of ketoprofen showed only weak reducing activity against 1,1-diphenyl-2-picrylhydrazyl radicals. No selective antiviral effects were noted for the tested compounds against a broad variety of DNA and RNA viruses. [Copyright &y& Elsevier]