α-(phenylselenenyl) ketones -: structure, molecular modelling and rationalization of their glutathione peroxidase-like activity

The crystal structures of four glutathione peroxidase mimetics- 1-(4-nitrophenyl)-2-(phenylselenenyl)ethanone (1), 2-(phenylselenenyl)-1-(2-thienyl)ethanone (3), 1-(2-naphthyl)-2-(phenylselenenyl)ethanone (4) and 1-(4-methoxyphenyl)-2-(phenylselenenyl)ethanone (5)-are reported. Theoretical calculations at the Hartree-Fock level of theory were performed for 1 and 5, and some other alpha-(phenylselenyl) ketones to elucidate the relationship between the glutathione peroxidase-like activity and the electronic effects of the functionalities attached to the keto group. As calculated on the basis of isodesmic reactions, the relative reactivities of the compounds were in satisfactory agreement with the observed glutathione peroxidase activities of the compounds. (C) 1998 Elsevier Science B.V. All rights reserved.