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From Cyclopentadiene to Isoxazoline‐Carbocyclic Nucleosides; Synthesis of Highly Active Inhibitors of Influenza A Virus H1N1
Author(s) -
Quadrelli Paolo,
Mella Mariella,
Legnani Laura,
AlSaad Dalya
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300119
Subject(s) - chemistry , cycloaddition , moiety , stereochemistry , nucleoside , quinoline , cyclopentadiene , influenza a virus , purine , virus , combinatorial chemistry , organic chemistry , virology , catalysis , biology , enzyme
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.