Synthesis of novel homo-N-nucleoside analogs composed of a homo-1,4-dioxane sugar analog and substituted 1,3,5-triazine base equivalents

Synthesis of novel homo-N-nucleoside analogs composed of a homo-1,4-dioxane sugar analog and substituted 1,3,5-triazine base equivalents

Enantioselective syntheses from dimethyl tartrate of 1,3,5-triazine homo-N-nucleoside analogs, containing a 1,4-dioxane moiety replacing the sugar unit in natural nucleosides, were accomplished. The triazine heterocycle in the nucleoside analogs was further substituted with combinations of NH(2), OH...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2008-12, Vol.13 (12), p.3092-3106
Hauptverfasser: Yu, Qiang, Schwidom, Dirk, Exner, Alexander, Carlsen, Per
Format: Artikel
Sprache:eng
Schlagworte:
4-Dioxane
5-Triazine
Cancer
Carbohydrates - chemical synthesis
Carbohydrates - chemistry
Dioxanes - chemical synthesis
Dioxanes - chemistry
Drug resistance
Heterocycle
Homo-N-nucleoside
Hydrogen bonds
Nucleoside analogs
Nucleoside analogue
Nucleosides - chemical synthesis
Nucleosides - chemistry
Sugar
Triazines - chemical synthesis
Triazines - chemistry
Uracil - chemistry
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Zusammenfassung:Enantioselective syntheses from dimethyl tartrate of 1,3,5-triazine homo-N-nucleoside analogs, containing a 1,4-dioxane moiety replacing the sugar unit in natural nucleosides, were accomplished. The triazine heterocycle in the nucleoside analogs was further substituted with combinations of NH(2), OH and Cl in the 2,4-triazine positions.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules13123092