Synthesis and Antiviral Evaluation of Some 3′‐Fluoro Bicyclic Nucleoside Analogues

Abstract

The synthesis of 3′‐fluoro analogues of recently discovered highly potent anti‐VZV furanopyrimidine deoxynucleosides (BCNAs) is herein reported, for both the alkyl and alkylphenyl series. The compounds are tested against a range of herpes viruses and display poor activity, strongly supporting the notion of the importance of the presence of a 3′‐OH for antiviral activity.

^†In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.

Keywords:

• VZV
• Bicyclic nucleoside analogues
• 3′‐OH

Acknowledgments

The authors are grateful to Mrs Anita Camps, Mr Steven Carmans, and Ms. Lies Vandenheurck for excellent technical assistance. This research was supported by grants from the Belgian Fonds voor Geneeskundig Wetenschappelijk Onderzoek, the Belgian Geconcerteerde Onderzoeksacties and The Leverhulme Trust. We also thank Helen Murphy for excellent secretarial assistance.

Notes

^†In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.

^aSelected experimental procedures and data for 3a–b: 3‐(2,3‐Dideoxy‐3‐fluoro‐β‐D‐ribofuranosyl)‐6‐(octyl)‐2,3‐dihydrofuro‐[2,3‐d]pyrimidin‐2‐one (3a).