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.

Chiacchio, U., Balestrieri, E., Macchi, B., Iannazzo, D., Piperno, A., Rescifina, A., et al. (2005). Synthesis of phosphonated carbocyclic 2 '-oxa-3 '-aza-nucleosides: Novel inhibitors of reverse transcriptase. JOURNAL OF MEDICINAL CHEMISTRY, 48(5), 1389-1394 [10.1021/jm049399i].

Synthesis of phosphonated carbocyclic 2 '-oxa-3 '-aza-nucleosides: Novel inhibitors of reverse transcriptase

BALESTRIERI, EMANUELA;MACCHI, BEATRICE;
2005-01-01

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.
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Rilevanza internazionale
Articolo
Esperti anonimi
Settore BIO/14
Settore CHIM/03 - Chimica Generale e Inorganica
English
Con Impact Factor ISI
5 fluoro 1 isoxazolidin 5 yl 1h pyrimidine 2,4 dione; antiretrovirus agent; carbocyclic 2' oxa 3' aza nucleoside; complementary DNA; diethyl [1' [4 amino 2 oxopyrimidin 1(2h) yl] 3' methyl 2' oxa 3' azacyclopent 4' yl]methylphosphonate; diethyl [1' [5 fluoro 2,4 dioxo 3,4 dihydropyrimidin 1(2h) yl] 3' methyl 2' oxa 3' azacyclopent 4' yl]methylphosphonate; diethyl [1' [[[5 methyl 2,4 dioxo 3,4 dihydropyrimidin 1(2h) yl]] 3' methyl 2' oxa 3' azacyclopent 4' yl]]methylphosphonate; isoxazolidine derivative; nucleoside analog; phosphonic acid derivative; RNA directed DNA polymerase; RNA directed DNA polymerase inhibitor; unclassified drug; virus RNA; zidovudine; antiviral activity; article; cell strain HL 60; cell strain U937; cytotoxicity; drug structure; drug synthesis; enzyme inhibition; Hepatitis B virus; human; human cell; Human immunodeficiency virus 1; lymphoid cell; nonhuman; proton nuclear magnetic resonance; Retrovirus; Antiviral Agents; Aza Compounds; Humans; Leukocytes, Mononuclear; Nitrogen Oxides; Nucleosides; Phosphonic Acids; Reverse Transcriptase Inhibitors; Stereoisomerism; Structure-Activity Relationship
Chiacchio, U., Balestrieri, E., Macchi, B., Iannazzo, D., Piperno, A., Rescifina, A., et al. (2005). Synthesis of phosphonated carbocyclic 2 '-oxa-3 '-aza-nucleosides: Novel inhibitors of reverse transcriptase. JOURNAL OF MEDICINAL CHEMISTRY, 48(5), 1389-1394 [10.1021/jm049399i].
Chiacchio, U; Balestrieri, E; Macchi, B; Iannazzo, D; Piperno, A; Rescifina, A; Romeo, R; Saglimbeni, M; Sciortino, M; Valveri, V; Mastino, A; Romeo, G
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/41896
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