Novel Acyclic Phosphonylated 1,2,3‐Triazolonucleosides with an Acetamidomethyl Linker: Synthesis and Biological Activity
Identifieur interne : 000A56 ( Main/Exploration ); précédent : 000A55; suivant : 000A57Novel Acyclic Phosphonylated 1,2,3‐Triazolonucleosides with an Acetamidomethyl Linker: Synthesis and Biological Activity
Auteurs : Iwona E. Głowacka [Pologne] ; Jan Balzarini [Belgique] ; Andrzej E. Wr Blewski [Pologne]Source :
- Archiv der Pharmazie [ 0365-6233 ] ; 2014-07.
Abstract
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 N3‐Bz‐benzuracil moiety showed activity against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cell cultures.
New 4‐substituted [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonates were synthesized as acyclic nucleotide analogs and tested for their antiviral activities against DNA and RNA viruses. [(1,2,3‐Triazol‐1‐yl)‐acetamido]methylphosphonate 6e (n = 1; R = N3‐Bz‐benzuracil) was found to be active against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cells.
Url:
DOI: 10.1002/ardp.201300468
Affiliations:
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Wr Blewski</name><affiliation wicri:level="1"><country xml:lang="fr">Pologne</country><wicri:regionArea>Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Łódź</wicri:regionArea><wicri:noRegion>Łódź</wicri:noRegion></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Archiv der Pharmazie</title><title level="j" type="alt">ARCHIV DER PHARMAZIE</title><idno type="ISSN">0365-6233</idno><idno type="eISSN">1521-4184</idno><imprint><biblScope unit="vol">347</biblScope><biblScope unit="issue">7</biblScope><biblScope unit="page" from="506">506</biblScope><biblScope unit="page" to="514">514</biblScope><biblScope unit="page-count">9</biblScope><date type="published" when="2014-07">2014-07</date></imprint><idno type="ISSN">0365-6233</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0365-6233</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract">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 N3‐Bz‐benzuracil moiety showed activity against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cell cultures.</div><div type="abstract">New 4‐substituted [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonates were synthesized as acyclic nucleotide analogs and tested for their antiviral activities against DNA and RNA viruses. [(1,2,3‐Triazol‐1‐yl)‐acetamido]methylphosphonate 6e (n = 1; R = N3‐Bz‐benzuracil) was found to be active against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cells.</div></front></TEI><affiliations><list><country><li>Belgique</li><li>Pologne</li></country></list><tree><country name="Pologne"><noRegion><name sortKey="Glowacka, Iwona E" sort="Glowacka, Iwona E" uniqKey="Glowacka I" first="Iwona E." last="Głowacka">Iwona E. Głowacka</name></noRegion><name sortKey="Glowacka, Iwona E" sort="Glowacka, Iwona E" uniqKey="Glowacka I" first="Iwona E." last="Głowacka">Iwona E. Głowacka</name><name sortKey="Wr Blewski, Andrzej E" sort="Wr Blewski, Andrzej E" uniqKey="Wr Blewski A" first="Andrzej E." last="Wr Blewski">Andrzej E. Wr Blewski</name></country><country name="Belgique"><noRegion><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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