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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
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 cyc...
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Published in: | Journal of carbohydrate chemistry 1999-01, Vol.18 (4), p.441-450 |
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Main Authors: | , , , , , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | 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. |
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ISSN: | 0732-8303 1532-2327 |
DOI: | 10.1080/07328309908544008 |