Synthesis and Hypnotic and Anti-Human Immunodeficiency Virus-1 Activities of N 3-Substituted 2’-Deoxy-2’-fluorouridines

Abstract

Reaction of (2) with diethylaminosulfur trifluoride in the presence of pyridine afforded 2’-deoxy-2 -fluororiboside 3a, from which 2’-deoxy-2’-fluorocytidine (4b) has been synthesized in good yield. Compound 3a was deprotected and subsequently treated with various benzyl halides or 2-chloro-4-fluoroacetophenone to give corresponding 5a—c and 6. Compounds 5a—c, as well as 6, showed weak hypnotic activity in mice. Compound 4b showed moderate antiviral activity against human immunodeficiency virus-1 but 3b, 5a—c, and 6 were virtually inactive. © 1994, The Pharmaceutical Society of Japan. All rights reserved.