The synthesis of isoxazolino-carbocyclic nornucleosides incorporating a quinoline moiety was tuned through nitrosocarbonyl intermediate chemistry, and a range of adenine analogues were attained through the linear construction of purine heterocyclic rings. The synthesis hinges on exo-selective 1,3-dipolar cycloaddition of quinolinenitrile oxide to the 2,3-oxazanorborn-5-enes and simple elaboration of the cycloadducts. The nucleoside derivatives were initially tested for their inhibitory activity against a variety of viruses, including HBV, PTV and Flu A virus H1N1. High antiviral activities were found for compounds 22aA and 22bA in the case of Flu A H1N1. The synthesis of nornucleosides incorporating a quinoline moiety was tuned through the application of nitrosocarbonyl group chemistry. The synthesis hinges on exo-selective 1,3-dipolar cycloaddition of quinolinenitrile oxide to 2,3-oxazanorborn-5-enes and elaboration of the cycloadducts. The nucleosides were tested as inhibitors of a variety of viruses and some were found highly active against Flu A H1N1.

Quadrelli, P., Mella, M., Legnani, L., Al-Saad, D. (2013). From Cyclopentadiene to Isoxazoline-Carbocyclic Nucleosides; Synthesis of Highly Active Inhibitors of Influenza A Virus H1N1. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013(21), 4655-4665 [10.1002/ejoc.201300119].

From Cyclopentadiene to Isoxazoline-Carbocyclic Nucleosides; Synthesis of Highly Active Inhibitors of Influenza A Virus H1N1

legnani, L;
2013

Abstract

The synthesis of isoxazolino-carbocyclic nornucleosides incorporating a quinoline moiety was tuned through nitrosocarbonyl intermediate chemistry, and a range of adenine analogues were attained through the linear construction of purine heterocyclic rings. The synthesis hinges on exo-selective 1,3-dipolar cycloaddition of quinolinenitrile oxide to the 2,3-oxazanorborn-5-enes and simple elaboration of the cycloadducts. The nucleoside derivatives were initially tested for their inhibitory activity against a variety of viruses, including HBV, PTV and Flu A virus H1N1. High antiviral activities were found for compounds 22aA and 22bA in the case of Flu A H1N1. The synthesis of nornucleosides incorporating a quinoline moiety was tuned through the application of nitrosocarbonyl group chemistry. The synthesis hinges on exo-selective 1,3-dipolar cycloaddition of quinolinenitrile oxide to 2,3-oxazanorborn-5-enes and elaboration of the cycloadducts. The nucleosides were tested as inhibitors of a variety of viruses and some were found highly active against Flu A H1N1.
Articolo in rivista - Articolo scientifico
Antiviral agents; Drug discovery; Inhibitors; Medicinal chemistry; Nucleosides;
English
4655
4665
11
Quadrelli, P., Mella, M., Legnani, L., Al-Saad, D. (2013). From Cyclopentadiene to Isoxazoline-Carbocyclic Nucleosides; Synthesis of Highly Active Inhibitors of Influenza A Virus H1N1. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013(21), 4655-4665 [10.1002/ejoc.201300119].
Quadrelli, P; Mella, M; Legnani, L; Al-Saad, D
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/351970
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