Homo Dinucleoside-α-hydroxyphosphonate Diesters as Prodrugs of the Antiviral Nucleoside Analogues 2',3'-Dideoxythymidine and 3'-Azido-2',3'-dideoxythymidine

Chris Meier; Lothar W. Habel; Wolfgang H.G. Laux; De Clercq Erik; Jan Balzarini

doi:10.1080/15257779508012466

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Homo Dinucleoside-α-hydroxyphosphonate Diesters as Prodrugs of the Antiviral Nucleoside Analogues 2',3'-Dideoxythymidine and 3'-Azido-2',3'-dideoxythymidine

Article 1995 en

Abstract

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Abstract The synthesis of a new prodrug system for antiviral nucleosides AZT (1) and ddT (2) based on α-hydroxybenzylphosphonates 3 is described. 3 hydrolyze via different mechanisms yielding the H-phosphonate monoesters 4 or nucleoside monophosphates 5, respectively. 3 were more lipophilic than 1, 2 and showed marked activity against HIV-1/2.

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Homo Dinucleoside-α-hydroxyphosphonate Diesters as Prodrugs of the Antiviral Nucleoside Analogues 2',3'-Dideoxythymidine and 3'-Azido-2',3'-dideoxythymidine

Abstract

Discussion(0)

Related publications

Lipophilic α‐hydroxybenzylphosphonates as prodrugs of 3′‐azido‐2′,3′‐dideoxythymidine (AZT)

5′,5′‐di‐<i>O</i>‐nucleosyl‐<i>O</i>′‐benzylphosphotriesters as potential prodrugs of 3′‐azido‐2′,3′‐dideoxythymidine‐5′‐monophosphate

Synthesis and Antiviral Activity of Some 5′-<i>N</i>-Phthaloyl-3′-Azido-2′,3′-Dideoxythymidine Analogues

Potential prodrug derivatives of 2',3'-didehydro-2',3'-dideoxynucleosides. Preparations and antiviral activities

Marked Inhibitory Activity of Masked Aryloxy Aminoacyl Phosphoramidate Derivatives of Dideoxynucleoside Analogues Against Visna Virus Infection