Abstract
2′,3′-Didesoxinucleosides, such as 3′-azido-3′-desoxitymidine (AZT), are known as powerful and selective inhibitors of the HIV replication. These compounds are phosphorylated inside the infected cell (in the cytoplasm) yielding the 2′,3′-didesoxinucleoside- 5′-phosphate that is able to bind to the virus DNA polymerases. Lack of the 3′-OH group prevents the 5′-3′-phosphodiester bonding which converts these compounds in DNA terminators. The structural similarity between 2′,3′-didesoxicarbonucleosides and 2′,3′- didesoxinucleosides led to the postulation that the former could display a similar antireplicative HIV activity. In this work we present a comparative structural study between 2′,3′-didesoxiuridine (I) and its carbocyclic derivatives (II-IV). The study includes several semi-empirical calculations (AMI and MNDO), aimed at a concrete description of the structural proximities between these groups of systems through charge distributions and distances between functional groups.
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© 1991 Plenum Press, New York
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Mosquera, R.A., Fernández, B., Vázquez, S.A., Uriarte, M.A.R.Y.E. (1991). A Structural Comparison of Potential Hiv Inhibitors: 2′,3′-Didesoxinucleosldes And 2′,3′-Didesoxicarbonucleosides. In: Jeffrey, G.A., Piniella, J.F. (eds) The Application of Charge Density Research to Chemistry and Drug Design. NATO ASI Series, vol 250. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3700-7_26
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DOI: https://doi.org/10.1007/978-1-4615-3700-7_26
Publisher Name: Springer, Boston, MA
Print ISBN: 978-0-306-43880-6
Online ISBN: 978-1-4615-3700-7
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