The synthesis of isoxazolino-carbocyclic nor-nucleosides incorporating an anthracene moiety was properly tuned through nitrosocarbonyl intermediates chemistry, and a variety of analogues were attained starting from stereodefined heterocyclic aminols through the linear construction of purine heterocyclic rings. The synthesis hinges on the exo selective 1,3-dipolar cycloaddition of the stable anthracenenitrile oxide to the N-benzoyl-2,3-oxazanorborn-5-ene and simple elaborations of the cycloadducts. A selection of nucleoside derivatives were initially tested for their inhibitory activity against a variety of viruses, including Hepatitis B and C, Human Papilloma virus as well as Influenza viruses of type A and B. Modest anti-viral activities were observed in Hepatitis assays while the activities in the cases of Influenza viruses were almost negligible. Good anti-viral activity was found for compound 11bC with no cellular toxicity at the dose tested in the case of Human Papilloma virus.

Moggio, Y., Legnani, L., Bovio, B., Memeo, M., Quadrelli, P. (2012). Synthesis of novel anthracene derivatives of isoxazolino-carbocyclic nucleoside analogues. TETRAHEDRON, 68(5), 1384-1392 [10.1016/j.tet.2011.12.047].

Synthesis of novel anthracene derivatives of isoxazolino-carbocyclic nucleoside analogues

LEGNANI, LAURA;
2012

Abstract

The synthesis of isoxazolino-carbocyclic nor-nucleosides incorporating an anthracene moiety was properly tuned through nitrosocarbonyl intermediates chemistry, and a variety of analogues were attained starting from stereodefined heterocyclic aminols through the linear construction of purine heterocyclic rings. The synthesis hinges on the exo selective 1,3-dipolar cycloaddition of the stable anthracenenitrile oxide to the N-benzoyl-2,3-oxazanorborn-5-ene and simple elaborations of the cycloadducts. A selection of nucleoside derivatives were initially tested for their inhibitory activity against a variety of viruses, including Hepatitis B and C, Human Papilloma virus as well as Influenza viruses of type A and B. Modest anti-viral activities were observed in Hepatitis assays while the activities in the cases of Influenza viruses were almost negligible. Good anti-viral activity was found for compound 11bC with no cellular toxicity at the dose tested in the case of Human Papilloma virus.
Articolo in rivista - Articolo scientifico
1,3-Dipolar cycloadditions; Anti-viral activity; Carbocyclic nucleosides; Conformational studies; Nitrosocarbonyl intermediates;
English
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1392
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Moggio, Y., Legnani, L., Bovio, B., Memeo, M., Quadrelli, P. (2012). Synthesis of novel anthracene derivatives of isoxazolino-carbocyclic nucleoside analogues. TETRAHEDRON, 68(5), 1384-1392 [10.1016/j.tet.2011.12.047].
Moggio, Y; Legnani, L; Bovio, B; Memeo, M; Quadrelli, P
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/351950
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