Synthesis and biological activity of 4 '-thio-1-xylofuranosyl purine nucleosides

A series of some new 4'-thio-L-xylofuranosyl nucleosides were prepared and evaluated as potential anticancer agents. A versatile sugar intermediate for direct coupling with the purine moiety is also synthesized by an efficient and high-yielding route. Proof of structure and configuration at all...

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Bibliographic Details
Published inNucleosides, nucleotides & nucleic acids Vol. 24; no. 10-12; pp. 1895 - 1906
Main Authors Tiwari, KN, Messini, L, Montgomery, JA, Secrist, JA
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 01.01.2005
Subjects
Biochemistry & Molecular Biology
Life Sciences & Biomedicine
Science & Technology
4 '-thionucleosides
nucleosides
T-ARAC
METABOLISM
ANALOGS
DNA
purines
antiviral activity
4'-THIO-BETA-D-ARABINOFURANOSYLCYTOSINE
OSI-7836
2-CHLORO-9-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)ADENINE
DFDC
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Summary:A series of some new 4'-thio-L-xylofuranosyl nucleosides were prepared and evaluated as potential anticancer agents. A versatile sugar intermediate for direct coupling with the purine moiety is also synthesized by an efficient and high-yielding route. Proof of structure and configuration at all chiral centers of the nucleosides was obtained by proton NMR. All target compounds were evaluated in a series of human cancer cell lines in vitro. The details of the synthesis of the carbohydrate precursor 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-L-xylofuranose (6) and corresponding purine nucleosides are presented in the manuscript.
Bibliography:NIH RePORTER
Medline
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770500269077