Phosphonated Nucleoside Analogues

Chapter 4 Phosphonated Nucleoside Analogues Roberto Romeo, Roberto Romeo Dipartimento Farmaco-Chimico, Università di Messina, Messina, ItalySearch for more papers by this authorCaterina Carnovale, Caterina Carnovale Dipartimento Farmaco-Chimico, Università di Messina, Messina, ItalySearch for more papers by this authorAntonio Rescifina, Antonio Rescifina Dipartimento di Scienze del Farmaco, Università di Catania, Catania, ItalySearch for more papers by this authorMaria Assunta Chiacchio, Maria Assunta Chiacchio Dipartimento di Scienze del Farmaco, Università di Catania, Catania, ItalySearch for more papers by this author Roberto Romeo, Roberto Romeo Dipartimento Farmaco-Chimico, Università di Messina, Messina, ItalySearch for more papers by this authorCaterina Carnovale, Caterina Carnovale Dipartimento Farmaco-Chimico, Università di Messina, Messina, ItalySearch for more papers by this authorAntonio Rescifina, Antonio Rescifina Dipartimento di Scienze del Farmaco, Università di Catania, Catania, ItalySearch for more papers by this authorMaria Assunta Chiacchio, Maria Assunta Chiacchio Dipartimento di Scienze del Farmaco, Università di Catania, Catania, ItalySearch for more papers by this author Book Editor(s):Pedro Merino, Pedro Merino Departamento de Síntesis y Estructura de Biomoléculas, y Departamento de Química Orgànica, Instituto de Sintesis y Catalisis Homogenea, Universidad de Zaragoza, CSIC, Zaragoza, Aragón, SpainSearch for more papers by this author First published: 15 February 2013 https://doi.org/10.1002/9781118498088.ch4Citations: 2 AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShareShare a linkShare onEmailFacebookTwitterLinkedInRedditWechat Summary Nucleoside analogues, in which the phosphoric ester group is replaced by the corresponding phosphonomethyl group, represent an important class of compounds endowed with potent antiviral activity. This modification confers on the molecule particular stability toward enzymatic degradation by phosphatases, making it possible to overcome the first limiting phosphorylation step. In this chapter, attention is directed to the carbocyclic and acyclic phosphonate nucleoside analogues. The various types of acyclic nucleoside phosphonates are illustrated. Acyclic phosphonated nucleosides (ANPs) have emerged as lead compounds. Their development has resulted in three approved drugs, and research on ANPs continues to provide new active derivatives. To achieve better oral uptake, the synthesis of prodrugs is often required. The increasing availability of prodrug options suggests the exploration of phosphonic acids in the search for new, efficient antiviral agents. References (a) Parker, W. B. Chem. Rev. 2009, 109, 2880–2893; 10.1021/cr900028p CASPubMedWeb of Science®Google Scholar (b) Liu, G.; Pranssen, E.; Fitch, E. F.; Warnew, E. J.Clin. 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