SYNTHESIS OF POTENTIAL ANTIRADIATION AGENTS FROM 3-SUBSTITUTED 2-OXAZOLIDINOMES DERIVED FROM PHENOL BENZENETHIOL AND RELATED COMPOUNDS

The HBr cleavage of 3-substituted 2-oxazolidinones was effectively applied in the synthesis of N-substituted and N,S-disubstituted derivatives of 2-aminoethanethiol in which the N substituent is a 2-phenoxy-, (phenylthio)-, (phenylsulfonyl)-, or (2-pyridylthio)ethyl or a correspondingly 3-substituted propyl group. None of these modifications of the amino group led to radioprotective activity approaching that of the parent compounds. Among the thiols, disulfides, thiosulfates, and phosphorothioates prepared, the following were slightly radioprotective in mice: sodium S-2-(2-phenoxyethylamino)ethyl hydrogen phosphorothioate (4c), S-2-[2-(phenylthio)-ethylamino]ethyl hydrogen thiosulfate (4g), S-2-[3-(phenylthio)propylamino]ethyl hydrogen thiosulfate (4j), N,N'-(dithiodiethylene)bis[3-(phenylthio)propylamine] dihydrochloride (5c), and lithium S-2-[3-(phenylsulfonyl) propylamino]ethyl hydrogen phosphorothioate (10c). N,N'-(Sulfonyldiethylene)bis(S-2-aminoethyl hydrogen thiosulfate) (7b), which was prepared by an aziridine ring-opening reaction, showed fair radioprotection. © 1969, American Chemical Society. All rights reserved.