title: Synthesis of phosphonated carbocyclic 2'-oxa-3'-aza-nucleosides: novel inhibitors of reverse transcriptase.
abstract: Phosphonated carbocyclic 2'-oxa-3'-aza-nucleosides have been synthesized in good yields by 1,3-dipolar cycloaddition methodology. The cytotoxicity and the reverse transcriptase inhibitory activity of the obtained compounds have been investigated. Phosphonated carbocyclic 2'-oxa-3'-aza-nucleosides, while showing low levels of cytotoxicity, exert a specific inhibitor activity on two different reverse transcriptases, which is comparable with that of AZT, opening new perspectives on their possible use as therapeutic agents, in anti-retroviral and anti-HBV chemotherapy.
authors.affiliation: Dipartimento Farmaco-Chimico, Università di Messina, Via SS. Annunziata, Messina 98168, Italy.
authors.forename: Ugo
authors.initials: U
authors.lastname: Chiacchio
authors.forename: Emanuela
authors.initials: E
authors.lastname: Balestrieri
authors.forename: Beatrice
authors.initials: B
authors.lastname: Macchi
authors.forename: Daniela
authors.initials: D
authors.lastname: Iannazzo
authors.forename: Anna
authors.initials: A
authors.lastname: Piperno
authors.forename: Antonio
authors.initials: A
authors.lastname: Rescifina
authors.forename: Roberto
authors.initials: R
authors.lastname: Romeo
authors.forename: Monica
authors.initials: M
authors.lastname: Saglimbeni
authors.forename: M Teresa
authors.initials: MT
authors.lastname: Sciortino
authors.forename: Vincenza
authors.initials: V
authors.lastname: Valveri
authors.forename: Antonio
authors.initials: A
authors.lastname: Mastino
authors.forename: Giovanni
authors.initials: G
authors.lastname: Romeo
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D006801:Humans; D066298:In Vitro Techniques; D007963:Leukocytes, Mononuclear / Q000187:drug effects / Q000201:enzymology; D009589:Nitrogen Oxides / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000998:Antiviral Agents; D001372:Aza Compounds; D009589:Nitrogen Oxides; D009705:Nucleosides; D063065:Organophosphonates; D018894:Reverse Transcriptase Inhibitors; C015388:nitrones