Tetrahedron p. 5537 - 5562 (1997)
Update date:2022-08-11
Topics:
Weaver, Richard
Gilbert, Ian H.
We describe the synthesis of a variety of lipophilic isosteres of nucleoside triphosphates as potential anti-HIV agents. The citrate molecule proved to be a good mimic of triphosphate by modelling in terms of charge and spatial distribution. Several lipophile derivatives of citrate were conjugated to the precedented anti-HIV nucleoside d4T via ester and amide linkages. A novel synthesis of 5'-amino-d4T is included. Intramolecular rearrangement of several amide-linked isosteres are also reported, along with an alternative synthetic strategy to the desired amide-linked isosteres.
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