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Synthesis and Biological Evaluation of 2-(2-Deoxy-β-D-ribofuranosyl)pyridine-4-carboxamide

✍ Scribed by Pieter E. Joos; Eddy L. Esmans; Roger A. Dommisse; André De Bruyn; Jan M. Balzarini; Eric D. De Clercq

Publisher
John Wiley and Sons
Year
1992
Tongue
German
Weight
549 KB
Volume
75
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A new protected 2‐deoxy‐D‐ribose derivative, 5‐O‐[(tert‐butyl)diphenylsilyl]‐2‐deoxy‐3,4‐O‐ isopropylidene‐aldehydo‐D‐ribose (5), was synthesized starting from 2‐deoxy‐D‐ribose. This compound was coupled with 2‐lithio‐4‐(4,5‐dihydro‐4,4‐dimethyloxazol‐2‐yl)pyridine giving a D/L‐glycero‐mixture 7 of 5‐O‐[(tert‐butyl)diphenylsilyl]‐2‐deoxy‐1‐C‐[4‐(4,5 ‐dihydro‐4,4‐dimethyloxazol‐2‐yl)pyridin‐2‐yl]‐3,4‐O‐isopropylidene‐ D‐erythro‐pentitol. The mixture 7 was 1‐O‐mesylated with methanesulfonyl chloride and subsequently treated with CF~3~COOH/H~2~O and ammonia to afford the α/β‐D‐anomers 10 of 2‐(2‐deoxy‐D‐ribofuranosyl)pyridine‐4‐carboxamide. Both anomers were purified and separated by HPLC and identified by NMR and DCI‐MS. Anomer β‐D‐10 was evaluated against a series of tumor‐cell lines and a variety of viral strains. No antitumor or antiviral activity was observed.

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