Thiosugars. XII. Synthesis of new 3'-O-substituted 2',5'-anhydro-2'-thio-alpha-D-pentofuranosyl nucleoside analogues.
Methyl 2,5-anhydro-3-O-(2-methoxyethyl)-2-thio-beta-D-arabinofuranoside and methyl 2,5-anhydro-3-O-(2-fluorobenzyl)-2-thio-alpha-D-lyxofuranoside were transformed into the corresponding uridine, thymidine, cytidine and adenosine analogues, which exclusively exhibited the alpha-configuration irrespective of the anomeric configuration of the donor. The structure, configuration, and conformation of the products was elucidated by X-ray structure analyses. The nucleoside analogues were tested for antiviral activities.
Voss
Jürgen
J
Institut für Organische Chemie der Universität Hamburg, Hamburg, Germany. voss@chemie.uni-hamburg.de
Wirsching
Jörn
J
Schulze
Oliver
O
Adiwidjaja
Gunadi
G
Giesler
Anja
A
Balzarini
Jan
J
De Clercq
Erik
E
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D018360:Crystallography, X-Ray; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000998:Antiviral Agents; D002241:Carbohydrates; D013438:Sulfhydryl Compounds