title: A new synthesis and an antiviral assessment of the 4'-fluoro derivative of 4'-deoxy-5'-noraristeromycin.
abstract: A synthetic route to (1S,2S,3R,5S)-3-(6-amino-9H-purin-9-yl)-5-fluorocyclopentane-1,2-diol (that is, the 4'-fluoro derivative of 4'-deoxy-5'-noraristeromycin, 3) is described via a fluorinated cyclopentanol, which is in contrast to existing schemes where fluorination occurred once the purine ring was present. Compound 3 was assayed versus a number of viruses. A favorable response was observed towards measles (IC(50) of 1.2 microg/mL in the neutral red assay and 14 microg/mL by the visual assay) but this was accompanied by cytotoxicity in the CV-1 host cells (21-36 microg/mL). Among the viruses unaffected by 3 were human cytomegalovirus and the poxviruses (vaccinia and cowpox), which are three viruses that were inhibited by the 4',4'-difluoro analog of 3 (that is, 2).
authors.affiliation: Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849, United States.
authors.forename: Xue-qiang
authors.initials: XQ
authors.lastname: Yin
authors.forename: Wei-kuan
authors.initials: WK
authors.lastname: Li
authors.forename: Minmin
authors.initials: M
authors.lastname: Yang
authors.forename: Stewart W
authors.initials: SW
authors.lastname: Schneller