title: 6'-Methyl-5'-homoaristeromycin: a structural variation of the anti-orthopox virus candidate 5'-homoaristeromycin.
abstract: The synthesis of 6'-methyl-5'-homoaristeromycin is described from a known 6'-ethyl ester. Antiviral analysis showed the (S)-6' stereoisomer retained the vaccinia activity of the parent 5'-homoaristeromycin (1) while the (R)-6' isomer was less active. Both were weaker than 1 towards cowpox. The diastereomers were equally active versus Epstein Barr virus while (S)-6' was three times more active toward vesicular stomatitis virus than (R)-6'. The diastereomers were inactive towards numerous other viruses. The CC50 for both diastereomers was >300μM.
authors.affiliation: The Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, United States.
authors.forename: Minmin
authors.initials: M
authors.lastname: Yang
authors.forename: Wei
authors.initials: W
authors.lastname: Ye
authors.forename: Stewart W
authors.initials: SW
authors.lastname: Schneller
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D007536:Isomerism; D015394:Molecular Structure; D018155:Orthopoxvirus / Q000187:drug effects*
chemical_list: C500020:5'-homoaristeromycin; D000998:Antiviral Agents; D000241:Adenosine