Characterization of lassa virus cell entry inhibitors: determination of the active enantiomer by asymmetric synthesis.

Détails

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Etat: Public
Version: de l'auteur
ID Serval
serval:BIB_B3838AA1DF7C
Type
Article: article d'un périodique ou d'un magazine.
Collection
Publications
Titre
Characterization of lassa virus cell entry inhibitors: determination of the active enantiomer by asymmetric synthesis.
Périodique
Bioorganic and Medicinal Chemistry Letters
Auteur(s)
Whitby L.R., Lee A.M., Kunz S., Oldstone M.B., Boger D.L.
ISSN
1464-3405 (Electronic)
ISSN-L
0960-894X
Statut éditorial
Publié
Date de publication
2009
Peer-reviewed
Oui
Volume
19
Numéro
14
Pages
3771-3774
Langue
anglais
Résumé
The comparative characterization of a series of 4-acyl-1,6-dialkylpiperazin-2-ones as potent cell entry inhibitors of the hemorrhagic fever arenavirus Lassa (LASV) is disclosed. The resolution and examination of the individual enantiomers of the prototypical LASV cell entry inhibitor 3 (16G8) is reported and the more potent (-)-enantiomer was found to be 15-fold more active than the corresponding (+)-enantiomer. The absolute configuration of (-)-3 was established by asymmetric synthesis of the active inhibitor (-)-(S)-3 (lassamycin-1). A limited deletion scan of lassamycin-1 defined key structural features required of the prototypical inhibitors.
Mots-clé
Antiviral Agents/chemical synthesis, Antiviral Agents/chemistry, Benzofurans/chemical synthesis, Benzofurans/chemistry, Cell Line, Tumor, Humans, Lassa virus/drug effects, Piperazines/chemical synthesis, Piperazines/chemistry, Stereoisomerism, Virus Internalization/drug effects
Pubmed
Création de la notice
17/04/2013 17:02
Dernière modification de la notice
20/08/2019 15:22
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