Synthesis, Conformation Analysis and Biological Evaluation of 2-(2,3-Dideoxy-ß-D-ribofuranosyl)pyridine-4-carboxamide
Article 1996 en
Authors
PJ
Pieter Joos
EE
Eddy L. Esmans
FA
F. C. Alderweireldt
Abstract
1 min read
2-(2,3-Dideoxy-P-~-ribofuranosyl)pyridine-4-carboxamide (2) was synthesized starting from the protected sugar analogue (3).Coupling of this compound with 2-lithio-4-(4,5-dihydro-4,4-dimethyloxazol-2-yl)pyridine (4).subsequent mesylation, reduction, deprotection and ammonolysis gave (2) as an anomeric mixture.&$-Separation was done by semi preparative hplc on a Lichrosorb 10 RP 8 column.In addition 2D-NOESY nmr spectroscopy was used for the assignment of the a/$-anomers of (2).High resolution 'H nmr allowed us to do a conformation analysis of compound (0-2).Finally the p-anomer of (2) was evaluated for its biological activity.
Marc Belmans, I. Vrijens, Eddy L. Esmans, R. Dommisse, J. A. Lepoivre, F. C. Alderweireldt, L. B. TOWNSEND, Linda L. Wotring, Jan Balzarini, De Clercq Erik
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