title: 1-(3-cyano-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine (cyanothymidine): synthesis and antiviral evaluation against human immunodeficiency virus.
abstract: 1-(3-Cyano-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine (cyanothymidine) (3a) has been prepared by an unambiguous route starting from D-xylose. The relative and absolute stereochemistry of 3a and its anomeric isomer 9 have been confirmed by NOE experiments and by X-ray diffraction analysis. In antiviral tests vs HIV 3a was shown to be inactive, a surprising result in view of a preliminary disclosure claiming potent anti-HIV activity. The activity previously assigned to 3a is believed to be due to contamination of that sample with the known antiviral nucleoside analogue 5b.
authors.affiliation: Pfizer Central Research, Sandwich, Kent, United Kingdom.
authors.forename: C W
authors.initials: CW
authors.lastname: Greengrass
authors.forename: D W
authors.initials: DW
authors.lastname: Hoople
authors.forename: S D
authors.initials: SD
authors.lastname: Street
authors.forename: F
authors.initials: F
authors.lastname: Hamilton
authors.forename: M S
authors.initials: MS
authors.lastname: Marriott
authors.forename: J
authors.initials: J
authors.lastname: Bordner
authors.forename: A G
authors.initials: AG
authors.lastname: Dalgleish
authors.forename: H
authors.initials: H
authors.lastname: Mitsuya
authors.forename: S
authors.initials: S
authors.lastname: Broder
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D008958:Models, Molecular; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014961:X-Ray Diffraction
chemical_list: D000998:Antiviral Agents; C058711:cyanothymidine; D013936:Thymidine