Synthesis and anti-hiv activity of further examples of l-[3-deoxy-3-(n-hydroxyamino)-β-d-threo- (and β-d-erythro)-pentofuranosyl]thymine derivatives1

Jean M J Tronchet, Martina Zsály, Olivier Lassout, Francoise Barbalat-Rey, I. Komáromi

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Abstract

Upon sodium cyanoborohydride reduction followed by de-O-silylation, the O-methyloxime and N-benzylnitrone of 5-TBDMS-3’-ketothymidine gave resolvable epimeric mixtures of l-[2, 3-dideoxy-3-(N-methoxyamino)-β-D-threo-and β-D-erythro-pentofuranosyl]thymine and l-[3-(N-benzyl-N-hydroxyamino)-2, 3-dideoxy-β-D-threo-and β-D-erythro-pentofuranosyl]thymine respectively. These compounds were inactive against HIV. On the other hand, l-[2, 3-dideoxy-3-(N-hydroxyamino)-5-0-TBDMS-β-D-tftra)-pentofuranosyl]thymine, upon treatment with acetone, then de-O-silylation, gave the bicyclonucleoside analogue 15, slightly more active against HIV in vitro than DDI.

Original languageEnglish
Pages (from-to)575-588
Number of pages14
JournalJournal of Carbohydrate Chemistry
Volume14
Issue number4-5
DOIs
Publication statusPublished - May 1 1995

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Thymine
HIV
Acetone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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Synthesis and anti-hiv activity of further examples of l-[3-deoxy-3-(n-hydroxyamino)-β-d-threo- (and β-d-erythro)-pentofuranosyl]thymine derivatives1 . / Tronchet, Jean M J; Zsály, Martina; Lassout, Olivier; Barbalat-Rey, Francoise; Komáromi, I.

In: Journal of Carbohydrate Chemistry, Vol. 14, No. 4-5, 01.05.1995, p. 575-588.

Research output: Contribution to journalArticle

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abstract = "Upon sodium cyanoborohydride reduction followed by de-O-silylation, the O-methyloxime and N-benzylnitrone of 5-TBDMS-3’-ketothymidine gave resolvable epimeric mixtures of l-[2, 3-dideoxy-3-(N-methoxyamino)-β-D-threo-and β-D-erythro-pentofuranosyl]thymine and l-[3-(N-benzyl-N-hydroxyamino)-2, 3-dideoxy-β-D-threo-and β-D-erythro-pentofuranosyl]thymine respectively. These compounds were inactive against HIV. On the other hand, l-[2, 3-dideoxy-3-(N-hydroxyamino)-5-0-TBDMS-β-D-tftra)-pentofuranosyl]thymine, upon treatment with acetone, then de-O-silylation, gave the bicyclonucleoside analogue 15, slightly more active against HIV in vitro than DDI.",
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AU - Zsály, Martina

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AU - Barbalat-Rey, Francoise

AU - Komáromi, I.

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N2 - Upon sodium cyanoborohydride reduction followed by de-O-silylation, the O-methyloxime and N-benzylnitrone of 5-TBDMS-3’-ketothymidine gave resolvable epimeric mixtures of l-[2, 3-dideoxy-3-(N-methoxyamino)-β-D-threo-and β-D-erythro-pentofuranosyl]thymine and l-[3-(N-benzyl-N-hydroxyamino)-2, 3-dideoxy-β-D-threo-and β-D-erythro-pentofuranosyl]thymine respectively. These compounds were inactive against HIV. On the other hand, l-[2, 3-dideoxy-3-(N-hydroxyamino)-5-0-TBDMS-β-D-tftra)-pentofuranosyl]thymine, upon treatment with acetone, then de-O-silylation, gave the bicyclonucleoside analogue 15, slightly more active against HIV in vitro than DDI.

AB - Upon sodium cyanoborohydride reduction followed by de-O-silylation, the O-methyloxime and N-benzylnitrone of 5-TBDMS-3’-ketothymidine gave resolvable epimeric mixtures of l-[2, 3-dideoxy-3-(N-methoxyamino)-β-D-threo-and β-D-erythro-pentofuranosyl]thymine and l-[3-(N-benzyl-N-hydroxyamino)-2, 3-dideoxy-β-D-threo-and β-D-erythro-pentofuranosyl]thymine respectively. These compounds were inactive against HIV. On the other hand, l-[2, 3-dideoxy-3-(N-hydroxyamino)-5-0-TBDMS-β-D-tftra)-pentofuranosyl]thymine, upon treatment with acetone, then de-O-silylation, gave the bicyclonucleoside analogue 15, slightly more active against HIV in vitro than DDI.

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