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Vandendriessche, F; Snoeck, R; Janssen, G; Hoogmartens, J; Van Aerschot, A; De Clercq, E; Herdewijn, P
Journal of medicinal chemistry, 04/1992, Letnik: 35, Številka: 8Journal Article
Optically pure acyclic nucleoside analogues with a 3(S),5-dihydroxypentyl or 4(R)-methoxy-3(S),5-dihydroxypentyl side chain were synthesized starting from 2-deoxy-D-ribose. The acyclic nucleosides were obtained by alkylation of the bases with the mesylates 16 and 17. Of these series of novel nucleoside analogues only 9-3(S),5-dihydroxypent-1-ylguanine (6d) showed marked antiviral activity. It inhibited the cytopathogenicity of herpes simplex virus type 1 (HSV-1) at a concentration of 0.4-0.6 microgram/mL, which thus points to a greater antiviral activity than recently reported for the mixture of the R and S enantiomers (12.5 micrograms/mL). In contrast with 6d, its 4(R)-methoxy derivative 7d did not show antiviral activity, which implies that the 4'-methoxy group is unable to mimic the 1',4'-oxygen bridge of the normal furanose ring.
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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in: SICRIS
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