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4‐Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation
Author(s) -
Mantione Daniele,
Aizpuru Olatz Olaizola,
Memeo Misal Giuseppe,
Bovio Bruna,
Quadrelli Paolo
Publication year - 2016
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.201501406
Subject(s) - chemistry , pyrimidine , uracil , nucleoside , cytidine , thymine , purine , cyclopentenone , stereochemistry , nucleophilic substitution , nucleotide , combinatorial chemistry , organic chemistry , biochemistry , dna , gene , enzyme
Racemic 4‐oxocyclopent‐2‐en‐1‐yl acetate was used in a short synthesis of nucleoside analogues with pyrimidine and purine heterobases. The protocol is based on a typical nucleophilic substitution process. Uracil, thymine, 6‐chloropurine, and some adenines gave the expected 4‐heterosubstituted products along with the isomeric 2‐heterosubstituted compounds as minor components. Samples of selected products were evaluated for their antiviral activity in a primary screening against a variety of viruses belonging to different classes. One of the compounds was found to be highly active against human papilloma virus (HPV).