SYNTHESIS OF BRAIN-TARGETED 5-IODO-2'-DEOXYURIDINE, 5-VINYL-2'-DEOXYURIDINE AND (E)-5-(2-IODOVINYL)-2'-DEOXYURIDINE COUPLED TO A DIHYDROPYRIDINE REVERSIBLE-ARROW PYRIDINIUM SALT REDOX CHEMICAL DELIVERY SYSTEM

5-Iodo-3'-O-(1-methyl-1,4-dihydropyridyl-3-carbonyl)-2'-deoxyuridine (15a), 5-vinyl-3'-O-(1-methyl-1,4-dihydropyridyl-3-carbonyl)-2'-deoxyuridine (15b) and (E)-5-(2-iodovinyl)-3'-O-(1-methyl-1,4-dihydropyridyl-3-carbonyl)-2'-deoxyuridine (15c) were synthesized for future evaluation as lipophilic brain-selective antiviral agents for the treatment of herpes simplex encephalitis. Quaternization of the 3'-O-(3-pyridylcarbonyl) compounds 10-11 using iodomethane afforded the corresponding 1-methylpyridinium salts 12-13 which were reduced with sodium dithionite to yield the corresponding 3'-O-(1-methyl-1,4-dihydropyridyl-3-carbonyl) compounds 14-15.