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Synthesis of 1,2-annulated adamantane heterocycles: structural determination studies of a bioactive cyclic sulfite |
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| Authors: | Grigoris Zoidis Lieve Naesens Emmanuel Mikros |
| Affiliation: | a Faculty of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Panepistimioupoli-Zografou, GR-15771 Athens, Greece b Institute of Biology NCSR ‘Demokritos’, GR-15310 Athens, Greece c Rega Institute, Department of Microbiology and Immunology, Katholieke Universiteit Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium |
| Abstract: | The novel heterocycle 3-oxatetracyclo[5.3.1.15,9.02,5]dodecane 4 is prepared by a simple and effective method, involving synthesis of the corresponding 2-hydroxy-1-adamantanomethanol followed by its intramolecular cyclization with thionyl chloride, along with 4-oxo-adamantane-3,5,4-dioxathiane 5 in yields depending on the reaction temperature. Dioxathiane 5 was markedly active against vesicular stomatitis virus, its potency being 2.5-fold higher than that of (S)-9-(2,3-dihydroxypropyl)adenine. NMR data and theoretical calculations on sulfite 5 and the corresponding dioxane 6 suggest that S O is oriented equatorially. |
| Keywords: | Adamantane dioxathiane and oxetane Conformational analysis NMR Theoretical calculations Antiviral activity |
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