Synthesis and biological activity of 4'-thio-L-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 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.
Tiwari
Kamal N
KN
Southern Research Institute, Birmingham, Alabama 35255-5305, USA.
Messini
Lea
L
Montgomery
John A
JA
Secrist
John A
JA
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009369:Neoplasms / Q000188:drug therapy; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014777:Virus Diseases / Q000188:drug therapy; D014779:Virus Replication / Q000187:drug effects*; D014780:Viruses / Q000254:growth & development*; D014994:Xylose / Q000138:chemical synthesis / Q000737:chemistry
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D011684:Purine Nucleosides; D013457:Sulfur Compounds; D014994:Xylose