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Synthesis of brain‐targeted 5‐iodo‐, 5‐vinyl‐ and ( E )‐5‐(2‐iodovinyl)‐2′‐deoxyuridines coupled to a dihydropyridine ⇌ pyridinium salt redox chemical delivery system
Author(s) -
Kumar Rakesh,
Ji Gueijun,
Wiebe Leonard I.,
Knaus Edward E.
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280327
Subject(s) - chemistry , pyridinium , sodium dithionite , yield (engineering) , medicinal chemistry , dihydropyridine , stereochemistry , organic chemistry , materials science , metallurgy , calcium
5‐Iodo‐3′‐ O ‐(1‐methyl‐1,4‐dihydropyridyl‐3‐carbonyl)‐2′‐deoxyuridine (15a) , 5‐vinyl‐3′‐ O ‐(1‐methyl‐1,4‐di‐hydropyridyl‐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.