title: Enantiomerically pure phosphonated carbocyclic 2'-oxa-3'-azanucleosides: synthesis and biological evaluation.
abstract: Starting from enantiomeric pure 1-[(3S,5R)- and 1-[(3R,5S)-3-(hydroxymethyl)-2-methylisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-diones (-)7a and (+)7b, obtained by lipase-catalyzed resolution, pure diethyl{[(3S,5R)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (-)12a and diethyl{[(3R,5S)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (+)12b have been synthesized. The obtained compounds showed no cytotoxic activity versus the U937 cell line in comparison with AZT, and were poorly able to inhibit HIV infection in vitro.
authors.affiliation: Dipartimento Scienze del Farmaco e Prodotti per la Salute, Università di Messina, Via S.S. Annunziata, 98168 Messina, Italy. robromeo@unime.it.
authors.forename: Roberto
authors.initials: R
authors.lastname: Romeo
authors.affiliation: Dipartimento Scienze del Farmaco e Prodotti per la Salute, Università di Messina, Via S.S. Annunziata, 98168 Messina, Italy. ccarnovale@unime.it.
authors.forename: Caterina
authors.initials: C
authors.lastname: Carnovale
authors.affiliation: Dipartimento Scienze del Farmaco e Prodotti per la Salute, Università di Messina, Via S.S. Annunziata, 98168 Messina, Italy. sgiofre@unime.it.
authors.forename: Salvatore V
authors.initials: SV
authors.lastname: Giofrè
authors.affiliation: Dipartimento Scienze del Farmaco, Università di Catania, Viale A. Doria 6, 95125 Catania, Italy. giulimonci@hotmail.it.
authors.forename: Giulia
authors.initials: G
authors.lastname: Monciino
authors.affiliation: Dipartimento Scienze del Farmaco, Università di Catania, Viale A. Doria 6, 95125 Catania, Italy. ma.chiacchio@unict.it.
authors.forename: Maria A
authors.initials: MA
authors.lastname: Chiacchio
authors.affiliation: Istituto di Chimica Biomolecolare del CNR, Via P. Gaifami 18, 95126 Catania, Italy. claudia.sanfilippo@icb.cnr.it.
authors.forename: Claudia
authors.initials: C
authors.lastname: Sanfilippo
authors.affiliation: Dipartimento di Medicina dei Sistemi, Università di Roma "Tor Vergata", 00133 Roma, Italy. macchi@med.uniroma2.it.
authors.forename: Beatrice
authors.initials: B
authors.lastname: Macchi
mesh_terms: D006678:HIV / Q000187:drug effects; D015658:HIV Infections / Q000188:drug therapy* / Q000821:virology; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D020298:U937 Cells
chemical_list: D009705:Nucleosides; D063065:Organophosphonates