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Novel Acyclic Phosphonylated 1,2,3‐Triazolonucleosides with an Acetamidomethyl Linker: Synthesis and Biological Activity
Author(s) -
Głowacka Iwona E.,
Balzarini Jan,
Wróblewski Andrzej E.
Publication year - 2014
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201300468
Subject(s) - moiety , chemistry , phosphonate , hela , linker , stereochemistry , vesicular stomatitis virus , biological activity , dna , nucleobase , cycloaddition , nucleotide , combinatorial chemistry , organic chemistry , biochemistry , virus , in vitro , biology , virology , computer science , gene , catalysis , operating system
A new series of 4‐substituted [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonates as acyclic nucleotide analogs were synthesized from diethyl (2‐chloroacetamido)methylphosphonate via azidation followed by 1,3‐dipolar cycloaddition with selected alkynes derived from natural nucleobases or their mimetics. All compounds were tested for their antiviral activities against DNA and RNA viruses as well as for cytostatic activity or cytotoxicity. Among all tested compounds, [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonate 6e substituted with the N 3 ‐Bz‐benzuracil moiety showed activity against the vesicular stomatitis virus (EC 50 = 45 µM) in HeLa cell cultures.