• Home
  • Search Results
  • Synthesis of C-4'truncated phosphonated carbocyclic 2'-oxa-3'-azanucleosides as antiviral agents.

Synthesis of C-4'truncated phosphonated carbocyclic 2'-oxa-3'-azanucleosides as antiviral agents.

The Journal of organic chemistry (2010-04-17)
Anna Piperno, Salvatore V Giofrè, Daniela Iannazzo, Roberto Romeo, Giovanni Romeo, Ugo Chiacchio, Antonio Rescifina, Dorota G Piotrowska
ABSTRACT

A new template of C-4'-truncated phosphonated nucleosides (TPCOANs) has been obtained in good yields according to two different routes which exploit the reactivity of a phosphonated nitrone. The one-step procedure based on the 1,3-dipolar cycloaddition of a phosphonated nitrone with vinyl nucleobases leads to the unnatural alpha-nucleosides as the main adducts. On the other hand, the target beta-anomers have been obtained in high yield by a two-step procedure based on the 1,3-dipolar cycloaddition of a phosphonated nitrone with vinyl acetate followed by nucleosidation reaction. The reactivity of the phosphonated nitrone has been investigated trough quantum mechanical DFT calculations at the B3LYP/D95+(d,p) theory level. Preliminary biological assays show that beta-anomers of TPCOANs are able to inhibit the reverse transcriptase of different retroviruses at concentrations in the nanomolar range, with a potency comparable with that of tenofovir.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Vinyl acetate, contains 3-20 ppm hydroquinone as inhibitor, ≥99%
Supelco
Vinyl acetate, analytical standard
Supelco
Vinyl acetate, analytical standard
Supelco
Vinyl acetate solution, certified reference material, 5000 μg/mL in acetonitrile
Vinyl acetate, European Pharmacopoeia (EP) Reference Standard

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.