Chemical and Pharmaceutical Bulletin p. 595 - 598 (1994)
Update date:2022-08-17
Topics:
Sato
Utsumi
Maruyama
Kimura
Yamamoto
Richman
Reaction of 9-[3,5-di-O-(tetrahydropyran-2-yl)-β-D- arabinofuranosyl]uracil (2) with diethylaminosulfur trifluoride in the presence of pyridine afforded 2'-deoxy-2'-flouroriboside 3a, from which 2'- deoxy-2'-fluorocytidine (14b) 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 N3-substituted 2'-deoxy- 2'-fluorouridines 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.
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