Title: Synthesis of a new series of phosphonylated 1,2,3-triazoles as acyclic analogs of ribavirin
Authors: Głowacka, Iwona E ×
Balzarini, Jan
Wróblewski, Andrzej E #
Issue Date: Sep-2013
Publisher: VCH Verlagsgesellschaft mbH
Series Title: Archiv der Pharmazie vol:346 issue:9 pages:677-87
Article number: 10.1002/ardp.201300156
Abstract: A novel series of phosphonylated 1,2,3-triazoles as structural acyclic analogs of ribavirin, in which the 1,2,3-triazole ring was substituted at C4' with COOMe, CONH2 , CONHOH, and CH2 NHBoc groups, were synthesized from diethyl azidomethyl-, 2-azidoethyl-, 3-azidopropyl-, 4-azidobutyl-, 2-azido-1-hydroxyethyl-, 3-azido-2-hydroxypropyl-, 2-azidoethoxymethyl- and 2-azidoethoxyethylphosphonate. The efficient synthesis of diethyl azidomethylphosphonate from diethyl 4-nitrobenzenesulfonylmethylphosphonate employing the in situ formed azides is described. All synthesized compounds were evaluated in vitro for their inhibitory activity against a broad variety of RNA and DNA viruses. No antiviral activity was observed at 100 µM. Only compound 13g exhibited inhibitory effects on the proliferation of HeLa cells (IC50  = 169 ± 45 µM).
ISSN: 0365-6233
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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