Entry to the 2,5-epoxyimidazo[1,5-a][1,3]diazocine and 5,8-epoxy[1,2,3]triazolo[1,5-a][1,3]diazocine systems : Novel reversed cyclonucleoside analogues

Article abstract of DOI:10.1080/07328309908544008

5-Azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose was used to obtain two reversed nucleoside analogues with either the 5-aminoimidazol-4-carboxamide or 5-amino-1,2,3-triazol-4-carboxamide groups attached, through the N1 site, to the C5′ site of the sugar. When deprotected these two compounds cyclised spontaneously and regiospecifically to form a bond between the exocyclic nitrogen and the anomeric carbon of the sugar. These reversed cyclonucleoside analogues are respectively members of the 2,5-epoxyimidazo[1,5-a][1,3]diazocine and 5,8-epoxy[1,2,3]triazolo[1,5-a][1,3]diazocine systems, novel ring systems with therapeutic potential. The shape of the cyclised imidazole compound and its immediate precursor has been studied by molecular modelling.

Full text of DOI:10.1080/07328309908544008

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Journal of Carbohydrate Chemistry
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Entry to the 2,5-Epoxyimidazo[1,5-
a][1,3]Diazocine and 5,8-
Epoxy[1,2,3]Triazolo[1,5-a]
[1,3]Diazocine Systems : Novel
Reversed Cyclonucleoside Analogues
D.F. Ewing , G. Goethals , G. Mackenzie , P. Martin , G.
Ronco , L. Vanbaelinghem & P. Villa
a School of Chemistry , University of Hull , Hull HU6 7RX, UK
b Laboratoire de Chimie Organique et Cinétique , Université
de Picardie Jules Verne , 80039 Amiens, France
c School of Chemistry , University of Hull , Hull HU6 7RX, UK
d Laboratoire de Chimie Organique et Cinétique , Université
de Picardie Jules Verne , 80039 Amiens, France
e Laboratoire de Chimie Organique et Cinétique , Université
de Picardie Jules Verne , 80039 Amiens, France
f Laboratoire de Chimie Organique et Cinétique , Université
de Picardie Jules Verne , 80039 Amiens, France
g Laboratoire de Chimie Organique et Cinétique , Université
de Picardie Jules Verne , 80039 Amiens, France
Published online: 27 Feb 2008.
To cite this article: D.F. Ewing , G. Goethals , G. Mackenzie , P. Martin , G. Ronco , L.
Vanbaelinghem & P. Villa (1999) Entry to the 2,5-Epoxyimidazo[1,5-a][1,3]Diazocine
and 5,8-Epoxy[1,2,3]Triazolo[1,5-a][1,3]Diazocine Systems : Novel Reversed
Cyclonucleoside Analogues, Journal of Carbohydrate Chemistry, 18:4, 441-450, DOI:
10.1080/07328309908544008
To link to this article: http://dx.doi.org/10.1080/07328309908544008
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