4-Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation

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 produc...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-02, Vol.2016 (5), p.983-991
Main Authors: Mantione, Daniele, Aizpuru, Olatz Olaizola, Memeo, Misal Giuseppe, Bovio, Bruna, Quadrelli, Paolo
Format: Article
Language:English
Subjects:
Antiviral agents
Biological activity
Carbocycles
HIV
Human immunodeficiency virus
Human papillomavirus
Nucleobases
Nucleophilic substitution
Nucleosides
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Summary: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). Racemic 4‐oxocyclopent‐2‐en‐1‐yl acetate was used in a short synthesis of nucleoside analogues with pyrimidine and purine heterobases.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201501406