CovidV1, Istex, Corpus, bibRecord, 000854

Synthesis of a New Series of Phosphonylated 1,2,3‐Triazoles as Acyclic Analogs of Ribavirin

Identifieur interne : 000854 ( Istex/Corpus ); précédent : 000853; suivant : 000855

Synthesis of a New Series of Phosphonylated 1,2,3‐Triazoles as Acyclic Analogs of Ribavirin

Auteurs : Iwona E. Głowacka ; Jan Balzarini ; Andrzej E. Wr Blewski

Source :

Archiv der Pharmazie [ 0365-6233 ] ; 2013-09.

RBID : ISTEX:2A69A0E93AD5F138F0B6F072C6D593E482C4B17E

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:

https://api.istex.fr/ark:/67375/WNG-PGPWCS4G-F/fulltext.pdf

DOI: 10.1002/ardp.201300156

Links to Exploration step

ISTEX:2A69A0E93AD5F138F0B6F072C6D593E482C4B17E

Le document en format XML

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<profileDesc><abstract xml:lang="en" style="main"><p>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, CONH<hi rend="subscript">2</hi>
, CONHOH, and CH<hi rend="subscript">2</hi>
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 <hi rend="italic">in situ</hi>
 formed azides is described. All synthesized compounds were evaluated <hi rend="italic">in vitro</hi>
 for their inhibitory activity against a broad variety of RNA and DNA viruses. No antiviral activity was observed at 100 µM. Only compound <hi rend="bold">13g</hi>
 exhibited inhibitory effects on the proliferation of HeLa cells (IC<hi rend="subscript">50</hi>
 = 169 ± 45 µM).</p>
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<abstract style="graphical"><p>A novel series of phosphonylated 1,2,3‐triazoles as structural acyclic analogs of ribavirin were synthesized and evaluated <hi rend="italic">in vitro</hi>
 for their inhibitory activity against a variety of RNA and DNA viruses. No antiviral activity was observed at 100 μM. Only compound <hi rend="bold">13g</hi>
 exhibited inhibitory effects on the proliferation of HeLa cells with an IC<hi rend="subscript">50</hi> of 169 ± 45 μM. 
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<correspondenceTo><lineatedText><line><b>Correspondence:</b>
 Dr. Iwona E. Głowacka, Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, Łódź, Poland.</line>
<line><b>E‐mail:</b>
<email>iwona.glowacka@umed.lodz.pl</email>
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<line><b>Fax:</b>
 +48 42 678 83 98</line>
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<contentMeta><titleGroup><title type="main">Synthesis of a New Series of Phosphonylated 1,2,3‐<fc>T</fc>
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<title type="short">Novel Phosphonylated 1,2,3‐<fc>T</fc>
riazoles as Ribavirin Analogs</title>
<title type="shortAuthors">I. E. Głowacka <i>et al.</i>
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<abstractGroup><abstract type="main" xml:lang="en"><section xml:id="ardp201300156-sec-0001"><p>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, CONH<sub>2</sub>
, CONHOH, and CH<sub>2</sub>
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 <i>in situ</i>
 formed azides is described. All synthesized compounds were evaluated <i>in vitro</i>
 for their inhibitory activity against a broad variety of RNA and DNA viruses. No antiviral activity was observed at 100 µM. Only compound <b>13g</b>
 exhibited inhibitory effects on the proliferation of HeLa cells (IC<sub>50</sub>
 = 169 ± 45 µM).</p>
</section>
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<abstract type="graphical"><p>A novel series of phosphonylated 1,2,3‐triazoles as structural acyclic analogs of ribavirin were synthesized and evaluated <i>in vitro</i>
 for their inhibitory activity against a variety of RNA and DNA viruses. No antiviral activity was observed at 100 μM. Only compound <b>13g</b>
 exhibited inhibitory effects on the proliferation of HeLa cells with an IC<sub>50</sub> of 169 ± 45 μM. 
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<abstract 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).</abstract>
<abstract type="graphical">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.</abstract>
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Synthesis of a New Series of Phosphonylated 1,2,3‐Triazoles as Acyclic Analogs of Ribavirin

Synthesis of a New Series of Phosphonylated 1,2,3‐Triazoles as Acyclic Analogs of Ribavirin

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