Synthesis and antiviral evaluation of 1,4-dioxane nucleoside analogs related to nucleoside dialdehydes

• Published in: Journal of medicinal chemistry Vol. 29; no. 12; pp. 2445 - 2450
• Main Author: Prisbe, Ernest J
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.12.1986
• Subjects: Antiviral Agents - chemical synthesis; Carbohydrates. Nucleosides and nucleotides; Cell Division; Cell Line; Chemistry; Dioxanes - chemical synthesis; Dioxanes - pharmacology; Exact sciences and technology; Indicators and Reagents; Magnetic Resonance Spectroscopy; Nucleosides - chemical synthesis; Nucleosides - pharmacology; Nucleosides, nucleotides and oligonucleotides; Organic chemistry; Parainfluenza Virus 3, Human - drug effects; Preparations and properties; Simplexvirus - drug effects; Structure-Activity Relationship; Vaccinia virus - drug effects; Antiviral; Purine nucleoside; NMR spectrum; Analog; Biological activity; Ultraviolet spectrum
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm00162a005

Since biologically active nucleoside 2',3'-dialdehydes exist as six-membered cyclic acetals (1) in solution, we have investigated the antiviral activity of some structurally similar 1,4-dioxane nucleoside analogues. By reacting 2',3'-seconucleoside tosylates with base, the guanine (10) and adenine (18) substituted (hydroxymethyl)dioxanes have been constructed. In addition, an unusual adenine-substituted divinyl ether (22) was synthesized via a base-catalyzed, double elimination of a 2',3'-di-O-tosyl-2',3'-secoadenosine. None of these compounds showed significant antiviral activity.