Synthesis and biological activity of 4'-thio-L-xylofuranosyl nucleosides.
A series of 4'-thio-L-xylofuranosyl nucleosides were prepared and evaluated as potential anticancer and antiviral agents. The details of a convenient and high-yielding synthesis of the carbohydrate precursor 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-L-xylofuranose (6) are presented. Proof of structure and configuration at all chiral centers of the nucleosides was obtained by proton and carbon NMR. All target compounds were evaluated in a series of human cancer cell lines in culture and as antiviral agents.
Tiwari
K N
KN
Southern Research Institute, P.O. Box 55305, Birmingham, Alabama 35255-5305, USA.
Messini
L
L
Montgomery
J A
JA
Secrist
J A
JA
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002236:Carbohydrate Conformation; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008826:Microbial Sensitivity Tests; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D014994:Xylose / Q000031:analogs & derivatives*
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D013872:Thionucleosides; D014994:Xylose