Synthesis of a New Series of Phosphonylated 1,2,3‐Triazoles as Acyclic Analogs of Ribavirin
Identifieur interne : 000B27 ( Main/Exploration ); précédent : 000B26; suivant : 000B28Synthesis of a New Series of Phosphonylated 1,2,3‐Triazoles as Acyclic Analogs of Ribavirin
Auteurs : Iwona E. Głowacka [Pologne] ; Jan Balzarini [Belgique] ; Andrzej E. Wr Blewski [Pologne]Source :
- Archiv der Pharmazie [ 0365-6233 ] ; 2013-09.
English descriptors
- Teeft :
- Anal, Analog, Angew, Antiviral, Azidophosphonate, Bioorg, Calcd, Cd3od, Cdcl3, Cell cultures, Ch2nhboc, Chem, Column chromatography, Conh2, Cooch3, Cytostatic, Diethyl, General procedure, Gmbh, Hela, Kgaa, Lett, Methyl propiolate, Mmol, Nucleoside, Pccc, Pccchahb, Pcch2, Pcchahb, Pch2, Pchahb, Pharm, Phosphonate, Phosphonylated, Pocc, Propiolate, Ribavirin, Ribavirin analogs, Silica, Test compounds, Verlag, Verlag gmbh, Weinheim, White powder.
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 CH2NHBoc 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).
A novel series of phosphonylated 1,2,3‐triazoles as structural acyclic analogs of ribavirin were synthesized and evaluated in vitro for their inhibitory activity against a 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 with an IC50 of 169 ± 45 μM.
Url:
DOI: 10.1002/ardp.201300156
Affiliations:
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Wr Blewski</name><affiliation wicri:level="1"><country xml:lang="fr">Pologne</country><wicri:regionArea>Faculty of Pharmacy, Bioorganic Chemistry Laboratory, 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">346</biblScope><biblScope unit="issue">9</biblScope><biblScope unit="page" from="677">677</biblScope><biblScope unit="page" to="687">687</biblScope><biblScope unit="page-count">11</biblScope><date type="published" when="2013-09">2013-09</date></imprint><idno type="ISSN">0365-6233</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0365-6233</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="Teeft" xml:lang="en"><term>Anal</term><term>Analog</term><term>Angew</term><term>Antiviral</term><term>Azidophosphonate</term><term>Bioorg</term><term>Calcd</term><term>Cd3od</term><term>Cdcl3</term><term>Cell cultures</term><term>Ch2nhboc</term><term>Chem</term><term>Column chromatography</term><term>Conh2</term><term>Cooch3</term><term>Cytostatic</term><term>Diethyl</term><term>General procedure</term><term>Gmbh</term><term>Hela</term><term>Kgaa</term><term>Lett</term><term>Methyl propiolate</term><term>Mmol</term><term>Nucleoside</term><term>Pccc</term><term>Pccchahb</term><term>Pcch2</term><term>Pcchahb</term><term>Pch2</term><term>Pchahb</term><term>Pharm</term><term>Phosphonate</term><term>Phosphonylated</term><term>Pocc</term><term>Propiolate</term><term>Ribavirin</term><term>Ribavirin analogs</term><term>Silica</term><term>Test compounds</term><term>Verlag</term><term>Verlag gmbh</term><term>Weinheim</term><term>White powder</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">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 CH2NHBoc 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).</div><div type="abstract">A novel series of phosphonylated 1,2,3‐triazoles as structural acyclic analogs of ribavirin were synthesized and evaluated in vitro for their inhibitory activity against a 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 with an IC50 of 169 ± 45 μM.</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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