ALPHA-(PHENYLSELENENYL) KETONES - STRUCTURE, MOLECULAR MODELING AND RATIONALIZATION OF THEIR GLUTATHIONE PEROXIDASE-LIKE ACTIVITY

The crystal structures of four glutathione peroxidase mimetics- 1-(4-n itrophenyl)-2-(phenylselenenyl)ethanone (1), 2-(phenylselenenyl)-1-(2- thienyl)ethanone (3), 1-(2-naphthyl)-2-(phenylselenenyl)ethanone (4) a nd 1-(4-methoxyphenyl)-2-(phenylselenenyl)ethanone (5)-are reported. T heoretical calculations at the Hartree-Fock level of theory were perfo rmed for 1 and 5, and some other alpha-(phenylselenyl) ketones to eluc idate the relationship between the glutathione peroxidase-like activit y and the electronic effects of the functionalities attached to the ke to group. As calculated on the basis of isodesmic reactions, the relat ive reactivities of the compounds were in satisfactory agreement with the observed glutathione peroxidase activities of the compounds. (C) 1 998 Elsevier Science B.V. All rights reserved.