TY - JOUR
T1 - Novel bicyclic sugar modified nucleosides
T2 - synthesis, conformational analysis and antiviral evaluation
AU - Kifli, Nurolaini
AU - Htar, Thet Thet
AU - De Clercq, Erik
AU - Balzarini, Jan
AU - Simons, Claire
N1 - Funding Information:
One of us (N.K.) would like to thank the Brunei Ministry of Health for the award of a Ph.D. scholarship. We would also like to acknowledge the EPSRC Mass Spectrometry Centre, Swansea, UK for mass spectroscopy data and the Geconcerteerde Onderzoeksacties––Vlaanderen (GOA Krediet no 00/12) for financial support.
PY - 2004/6/15
Y1 - 2004/6/15
N2 - Methodology previously described by us was applied to the formation of novel conformationally restrained bicyclic sugar modified nucleosides, with introduction of an oxazole and a thiocarbamate ring at the 2′, 3′-positions of the ribonucleosides. Two novel alkyl derivatives of 2′,3′-dideoxy-2 ′,3′-oxazole-β-D-uridine and a novel uridine 2′,3′-thiocarbamate were successfully synthesised. Conformational evaluation of all the synthesised compounds was conducted using the theoretical potential energy calculation via the MACROMODEL V.6.0 molecular modelling programme. The conformationally restrained nucleosides described were evaluated against a wide range of DNA and RNA viruses. None of the compounds showed specific antiviral effects at subtoxic concentrations.
AB - Methodology previously described by us was applied to the formation of novel conformationally restrained bicyclic sugar modified nucleosides, with introduction of an oxazole and a thiocarbamate ring at the 2′, 3′-positions of the ribonucleosides. Two novel alkyl derivatives of 2′,3′-dideoxy-2 ′,3′-oxazole-β-D-uridine and a novel uridine 2′,3′-thiocarbamate were successfully synthesised. Conformational evaluation of all the synthesised compounds was conducted using the theoretical potential energy calculation via the MACROMODEL V.6.0 molecular modelling programme. The conformationally restrained nucleosides described were evaluated against a wide range of DNA and RNA viruses. None of the compounds showed specific antiviral effects at subtoxic concentrations.
KW - Antiviral activity
KW - Conformational analysis
KW - Conformationally restrained nucleosides
KW - Oxazole
KW - Thiocarbamate
UR - http://www.scopus.com/inward/record.url?scp=2542482709&partnerID=8YFLogxK
U2 - 10.1016/j.bmc.2004.03.072
DO - 10.1016/j.bmc.2004.03.072
M3 - Article
C2 - 15158793
AN - SCOPUS:2542482709
SN - 0968-0896
VL - 12
SP - 3247
EP - 3257
JO - Bioorganic & Medicinal Chemistry
JF - Bioorganic & Medicinal Chemistry
IS - 12
ER -