Stereocontrolled Facile Synthesis and Biological Evaluation of (3′S) and (3′R)-3′-Amino (and Azido)-3′-Deoxy Pyranonucleosides

  title={Stereocontrolled Facile Synthesis and Biological Evaluation of (3′S) and (3′R)-3′-Amino (and Azido)-3′-Deoxy Pyranonucleosides},
  author={Stella Manta and Vanessa Parmenopoulou and Christos Kiritsis and Athina Dimopoulou and Nikolaos Kollatos and Ioannis Papasotiriou and Jan Balzarini and Dimitri Komiotis},
  journal={Nucleosides, Nucleotides \& Nucleic Acids},
  pages={522 - 535}
This article describes the synthesis of (3 ′S) and (3 ′R)-3 ′-amino-3 ′-deoxy pyranonucleosides and their precursors (3 ′S) and (3 ′R)-3 ′-azido-3 ′-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesulfonyl-α-D-allofuranose followed by hydrolysis and subsequent acetylation afforded 3-azido-3-deoxy-1,2,4,6-tetra-O-acetyl-D-glucopyranose, which upon coupling with the proper silylated bases, deacetylation, and catalytic hydrogenation, obtained the target 3 ′-amino-3… 

Stereocontrolled Facile Synthesis and Biological Evaluation of (3′S) and (3′R)-3′-Amino (and Azido)-3′-deoxy Pyranonucleosides.

A variety of 3′-amino-3′-deoxypyranonucleosides and their 3′-azide precursors are designed, synthesized and evaluated for their biological activities.

Synthesis of novel N-acyl-β-d-glucopyranosylamines and ureas as potential lead cytostatic agents

Only analogue 6f weakly but significantly inhibited the replication of parainfluenza-3 virus, Sindbis virus and Coxsackie virus B4 in cell cultures at concentrations of 45–58 μM.



Synthesis and biological evaluation of 3'-C-ethynyl and 3'-C-(1,4-disubstituted-1,2,3-triazolo) double-headed pyranonucleosides.

The double-headed nucleoside derivatives 8a, 8c and 8e showed a moderate cytostatic activity against human cervix carcinoma HeLa cells which may be the basis for the synthesis of analogous derivatives with improved cytostatics potential.

Synthesis and Anti-HIV Activity of β-D-3′-Azido-2′,3′-unsaturated Nucleosides and β-D-3′-Azido-3′-deoxyribofuranosylnucleosides

An efficient method for the synthesis of nucleoside analogs bearing structural features of both AZT and d4T was described, from which a series of pyrimidine and purine nucleosides were synthesized in high yields and evaluated as potential anti-HIV agents.