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Paper | Special issue | Vol 42, No. 1, 1996, pp.173-187
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S1
Synthesis, Conformational Analysis and Biological Evaluation of 2-(5-Deoxy-β-D-ribofuranosyl)pyridine-4-carboxamide

Pieter E. Joos, Alex De Groot, Eddy L. Esmans, Frank C. Alderweireldt, André De Bruyn, Jan Balzarini, and Erik De Clercq

*University of Antwerp (RUCA), Department of Chemistry, Groenenborgerlaan 171, B-2020 Antwerp, Belgium

Abstract

Coupling of 5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone (5) with 2-lithio-4-(4,5-dihydro-4,4-dimethyloxazol-2-yl)pyridine (6), subsequent mesylation, followed by reduction and ammonolysis resulted in the formation of 2-(5-deoxy-β-D-ribofuranosyl)pyridine-4-carboxamide (4). The anomeric configuration was established with 2D-NOESY-1H-nmr-spectroscopy. Conformational analysis was done with the aid of the high resolution 1H-nmr-spectroscopy data. Compound (4) possessed modest cytostatic activity against a number of tumor cell lines and was slightly inhibitory to vaccinia virus and vesicular stomatitis virus.