Synthesis and antiviral evaluation of 1,4-dioxane nucleoside analogs related to nucleoside dialdehydes
- 1 December 1986
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 29 (12) , 2445-2450
- https://doi.org/10.1021/jm00162a005
Abstract
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.This publication has 12 references indexed in Scilit:
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