Literature DB >> 1619614

Synthesis and anti-HIV activity of isonucleosides.

D M Huryn1, B C Sluboski, S Y Tam, M Weigele, I Sim, B D Anderson, H Mitsuya, S Broder.   

Abstract

A series of isomeric 2',3'-dideoxynucleosides which contains a modified carbohydrate moiety has been prepared. This class of compounds was designed to mimic the activity of known anti-HIV dideoxynucleosides, while imparting enhanced chemical and enzymatic stability. Isonucleosides containing the standard heterocyclic bases (A, C, G, T) were synthesized via nucleophilic addition of the base to an isomeric sugar unit. Modified derivatives were generated by manipulation of the intact isonucleoside. Two of the compound prepared, iso-ddA (1) and iso-ddG (6), exhibit significant and selective anti-HIV activity, as well as beneficial hydrolytic stability.

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Year:  1992        PMID: 1619614     DOI: 10.1021/jm00091a001

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  4 in total

Review 1.  Antiviral activities of isometric dideoxynucleosides of D- and L-related stereochemistry.

Authors:  V Nair; T S Jahnke
Journal:  Antimicrob Agents Chemother       Date:  1995-05       Impact factor: 5.191

2.  Anti-human immunodeficiency virus activities of nucleosides and nucleotides: correlation with molecular electrostatic potential data.

Authors:  T Mickle; V Nair
Journal:  Antimicrob Agents Chemother       Date:  2000-11       Impact factor: 5.191

3.  Antiviral, metabolic, and pharmacokinetic properties of the isomeric dideoxynucleoside 4(S)-(6-amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol.

Authors:  V Nair; M H St Clair; J E Reardon; H C Krasny; R J Hazen; M T Paff; L R Boone; M Tisdale; I Najera; R E Dornsife
Journal:  Antimicrob Agents Chemother       Date:  1995-09       Impact factor: 5.191

4.  Synthesis and Biological Evaluation of Structurally Varied 5'-/6'-Isonucleosides and Theobromine-Containing N-Isonucleosidyl Derivatives.

Authors:  Nuno M Xavier; Eduardo C de Sousa; Margarida P Pereira; Anne Loesche; Immo Serbian; René Csuk; M Conceição Oliveira
Journal:  Pharmaceuticals (Basel)       Date:  2019-07-02
  4 in total

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