Nucleosides. CXLIII. Synthesis of 5'-deoxy-5'-substituted-2,2'-anhydro-1-(.BETA.-D-arabinofuranosyl)uracils. A new 2,5'- to 2,2'-anhydro-nucleoside transformation. Studies directed toward the synthesis of 2'-deoxy-2'-substituted arabino nucleosides.
- 1 January 1987
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 35 (11) , 4494-4497
- https://doi.org/10.1248/cpb.35.4494
Abstract
Treatment of 2,5''-anhydro-3''-O-acetyl-2''-O-triflyluridine with a nucleophile such as NaOAc, NaN3, LiCl or LiBr, did not afford the 2''-substituted 2,5''-anhydro-arabinosyluracil, but gave 2,2''-anhydro-1-(5-substituted-.beta.-D-arabinofuranosyl)uracil instead.This publication has 9 references indexed in Scilit:
- Activities of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine and its metabolites against herpes simplex virus types 1 and 2 in cell culture and in mice infected intracerebrally with herpes simplex virus type 2Antimicrobial Agents and Chemotherapy, 1986
- Nucleosides. 131. The Synthesis of 5-(2-Chloro-2-Deoxy-β-D-arabino-Furanosyl)Uracil. Reinterpretation of Reaction of ψ-Uridine With α-Acetoxyisobutyryl Chloride. Studies Directed Toward the Synthesis of 2′-Deoxy-2′-SubstitutedArabino-Nucleosides. 2Nucleosides, Nucleotides and Nucleic Acids, 1985
- Nucleosides. 132. Synthesis of 5-(2'-substituted-2'-deoxy-.beta.-D-arabinofuranosyl)-1-methyluracils from 1-methyl-.psi.-uridine. The first direct introduction of the 2'-substituent to C-2' in the "up" configuration by nucleophilic reactions. Studies directed toward the synthesis of 2'-deoxy-2'-substituted arabino nucleosides 3The Journal of Organic Chemistry, 1985
- Antiviral activity of 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl-5-iodocytosine against human cytomegalovirus in human skin fibroblastsAntimicrobial Agents and Chemotherapy, 1985
- Effects of Certain Nucleoside Analogues on Human Cytomegalovirus Replication in vitroJournal of General Virology, 1984
- Therapeutic activities of 1-(2-fluoro-2-deoxy-beta-D-arabinofuranosyl)-5-iodocytosine and -thymine alone and in combination with acyclovir and vidarabine in mice infected intracerebrally with herpes simplex virusAntimicrobial Agents and Chemotherapy, 1983
- PHASE-I EVALUATION OF 2'-FLUORO-5-IODO-1-BETA-D-ARABINOFURANOSYLCYTOSINE IN IMMUNOSUPPRESSED PATIENTS WITH HERPESVIRUS-INFECTION1983
- 2'-fluoro-5-iodo-aracytosine, a potent and selective anti-herpesvirus agentAntimicrobial Agents and Chemotherapy, 1980
- Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosidesJournal of Medicinal Chemistry, 1979