SrasV1, PascalFrancis, Checkpoint, bibRecord, 000491

Design and synthesis of dipeptidyl glutaminyl fluoromethyl ketones as potent severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors

Identifieur interne : 000491 ( PascalFrancis/Checkpoint ); précédent : 000490; suivant : 000492

Design and synthesis of dipeptidyl glutaminyl fluoromethyl ketones as potent severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors

Auteurs : Han-Zhong Zhang [États-Unis] ; HONG ZHANG [États-Unis] ; William Kemnitzer [États-Unis] ; Ben Tseng [États-Unis] ; Jindrich Jr Cinatl [Allemagne] ; Martin Michaelis [Allemagne] ; Hans Wilhelm Doerr [Allemagne] ; SUI XIONG CAI [États-Unis]

Source :

Journal of medicinal chemistry : (Print) [ 0022-2623 ] ; 2006.

RBID : Pascal:06-0304982

Descripteurs français

Pascal (Inist)
- Synthèse chimique, Dipeptide, Cétone, Syndrome respiratoire aigu sévère, Virus syndrome respiratoire aigu sévère, Antiviral, In vitro, Relation structure activité, Halogénocétone, Composé peptidomimétique, Fluor Composé organique, Peptide, Lignée cellulaire, Singe, Rein, Côlon, Homme, Lignée VERO, Lignée CACO2, Glutamine(N2-benzyloxycarbonylleucyl-1-désoxy-N5,N5-diméthyl-1-fluorométhyl).
Wicri :
- topic : Singe, Homme.

English descriptors

KwdEn :
- Antiviral, Cell line, Chemical synthesis, Colon, Dipeptides, Fluorine Organic compounds, Haloketone, Human, In vitro, Ketone, Kidney, Monkey, Peptides, Peptidomimetic compound, Severe acute respiratory syndrome, Severe acute respiratory syndrome virus, Structure activity relation.

Abstract

This paper describes the design and synthesis of dipeptidyl N,N-dimethyl glutaminyl fluoromethyl ketones (fmk) as severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors. The compounds were tested against SARS-CoV-induced cell death in Vero or CaCo2 cells as a measurement of the inhibiting effects of the compounds on the replication of the virus. Z-Leu-Gln(NMe₂)-fmk (6a) was found to be a potent inhibitor with low toxicity in cells, protecting cells with an EC₅₀ value of 2.5 μM and exhibiting a selectivity index of >40.

Affiliations:

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Le document en format XML

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<front><div type="abstract" xml:lang="en">This paper describes the design and synthesis of dipeptidyl N,N-dimethyl glutaminyl fluoromethyl ketones (fmk) as severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors. The compounds were tested against SARS-CoV-induced cell death in Vero or CaCo2 cells as a measurement of the inhibiting effects of the compounds on the replication of the virus. Z-Leu-Gln(NMe<sub>2</sub>
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<fC03 i1="06" i2="X" l="FRE"><s0>Antiviral</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG"><s0>Antiviral</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA"><s0>Antiviral</s0>
<s5>06</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE"><s0>In vitro</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG"><s0>In vitro</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA"><s0>In vitro</s0>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Relation structure activité</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG"><s0>Structure activity relation</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Relación estructura actividad</s0>
<s5>08</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Halogénocétone</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>Haloketone</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Halocetona</s0>
<s5>09</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>Composé peptidomimétique</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>Peptidomimetic compound</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>Compuesto peptidomimético</s0>
<s5>10</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE"><s0>Fluor Composé organique</s0>
<s2>NC</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG"><s0>Fluorine Organic compounds</s0>
<s2>NC</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA"><s0>Fluor Compuesto orgánico</s0>
<s2>NC</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>11</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>Peptide</s0>
<s5>32</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG"><s0>Peptides</s0>
<s5>32</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA"><s0>Péptido</s0>
<s5>32</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Lignée cellulaire</s0>
<s5>33</s5>
</fC03>
<fC03 i1="13" i2="X" l="ENG"><s0>Cell line</s0>
<s5>33</s5>
</fC03>
<fC03 i1="13" i2="X" l="SPA"><s0>Línea celular</s0>
<s5>33</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>Singe</s0>
<s5>34</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG"><s0>Monkey</s0>
<s5>34</s5>
</fC03>
<fC03 i1="14" i2="X" l="SPA"><s0>Mono</s0>
<s5>34</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE"><s0>Rein</s0>
<s5>35</s5>
</fC03>
<fC03 i1="15" i2="X" l="ENG"><s0>Kidney</s0>
<s5>35</s5>
</fC03>
<fC03 i1="15" i2="X" l="SPA"><s0>Riñón</s0>
<s5>35</s5>
</fC03>
<fC03 i1="16" i2="X" l="FRE"><s0>Côlon</s0>
<s5>36</s5>
</fC03>
<fC03 i1="16" i2="X" l="ENG"><s0>Colon</s0>
<s5>36</s5>
</fC03>
<fC03 i1="16" i2="X" l="SPA"><s0>Colón</s0>
<s5>36</s5>
</fC03>
<fC03 i1="17" i2="X" l="FRE"><s0>Homme</s0>
<s5>37</s5>
</fC03>
<fC03 i1="17" i2="X" l="ENG"><s0>Human</s0>
<s5>37</s5>
</fC03>
<fC03 i1="17" i2="X" l="SPA"><s0>Hombre</s0>
<s5>37</s5>
</fC03>
<fC03 i1="18" i2="X" l="FRE"><s0>Lignée VERO</s0>
<s4>INC</s4>
<s5>76</s5>
</fC03>
<fC03 i1="19" i2="X" l="FRE"><s0>Lignée CACO2</s0>
<s4>INC</s4>
<s5>77</s5>
</fC03>
<fC03 i1="20" i2="X" l="FRE"><s0>Glutamine(N2-benzyloxycarbonylleucyl-1-désoxy-N5,N5-diméthyl-1-fluorométhyl)</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>78</s5>
</fC03>
<fC07 i1="01" i2="X" l="FRE"><s0>Virose</s0>
</fC07>
<fC07 i1="01" i2="X" l="ENG"><s0>Viral disease</s0>
</fC07>
<fC07 i1="01" i2="X" l="SPA"><s0>Virosis</s0>
</fC07>
<fC07 i1="02" i2="X" l="FRE"><s0>Infection</s0>
</fC07>
<fC07 i1="02" i2="X" l="ENG"><s0>Infection</s0>
</fC07>
<fC07 i1="02" i2="X" l="SPA"><s0>Infección</s0>
</fC07>
<fC07 i1="03" i2="X" l="FRE"><s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="ENG"><s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="SPA"><s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="FRE"><s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="ENG"><s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="SPA"><s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="FRE"><s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="ENG"><s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="SPA"><s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="FRE"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="ENG"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="SPA"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="07" i2="X" l="FRE"><s0>Primates</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="07" i2="X" l="ENG"><s0>Primates</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="07" i2="X" l="SPA"><s0>Primates</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="08" i2="X" l="FRE"><s0>Mammalia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="08" i2="X" l="ENG"><s0>Mammalia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="08" i2="X" l="SPA"><s0>Mammalia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="09" i2="X" l="FRE"><s0>Vertebrata</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="09" i2="X" l="ENG"><s0>Vertebrata</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="09" i2="X" l="SPA"><s0>Vertebrata</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="10" i2="X" l="FRE"><s0>Appareil respiratoire pathologie</s0>
<s5>53</s5>
</fC07>
<fC07 i1="10" i2="X" l="ENG"><s0>Respiratory disease</s0>
<s5>53</s5>
</fC07>
<fC07 i1="10" i2="X" l="SPA"><s0>Aparato respiratorio patología</s0>
<s5>53</s5>
</fC07>
<fC07 i1="11" i2="X" l="FRE"><s0>Poumon pathologie</s0>
<s5>54</s5>
</fC07>
<fC07 i1="11" i2="X" l="ENG"><s0>Lung disease</s0>
<s5>54</s5>
</fC07>
<fC07 i1="11" i2="X" l="SPA"><s0>Pulmón patología</s0>
<s5>54</s5>
</fC07>
<fN21><s1>198</s1>
</fN21>
</pA>
</standard>
</inist>
<affiliations><list><country><li>Allemagne</li>
<li>États-Unis</li>
</country>
<region><li>District de Darmstadt</li>
<li>Hesse (Land)</li>
</region>
<settlement><li>Francfort-sur-le-Main</li>
</settlement>
</list>
<tree><country name="États-Unis"><noRegion><name sortKey="Zhang, Han Zhong" sort="Zhang, Han Zhong" uniqKey="Zhang H" first="Han-Zhong" last="Zhang">Han-Zhong Zhang</name>
</noRegion>
<name sortKey="Hong Zhang" sort="Hong Zhang" uniqKey="Hong Zhang" last="Hong Zhang">HONG ZHANG</name>
<name sortKey="Kemnitzer, William" sort="Kemnitzer, William" uniqKey="Kemnitzer W" first="William" last="Kemnitzer">William Kemnitzer</name>
<name sortKey="Sui Xiong Cai" sort="Sui Xiong Cai" uniqKey="Sui Xiong Cai" last="Sui Xiong Cai">SUI XIONG CAI</name>
<name sortKey="Tseng, Ben" sort="Tseng, Ben" uniqKey="Tseng B" first="Ben" last="Tseng">Ben Tseng</name>
</country>
<country name="Allemagne"><region name="Hesse (Land)"><name sortKey="Cinatl, Jindrich Jr" sort="Cinatl, Jindrich Jr" uniqKey="Cinatl J" first="Jindrich Jr" last="Cinatl">Jindrich Jr Cinatl</name>
</region>
<name sortKey="Doerr, Hans Wilhelm" sort="Doerr, Hans Wilhelm" uniqKey="Doerr H" first="Hans Wilhelm" last="Doerr">Hans Wilhelm Doerr</name>
<name sortKey="Michaelis, Martin" sort="Michaelis, Martin" uniqKey="Michaelis M" first="Martin" last="Michaelis">Martin Michaelis</name>
</country>
</tree>
</affiliations>
</record>

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   |texte=   Design and synthesis of dipeptidyl glutaminyl fluoromethyl ketones as potent severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors
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Design and synthesis of dipeptidyl glutaminyl fluoromethyl ketones as potent severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors

Design and synthesis of dipeptidyl glutaminyl fluoromethyl ketones as potent severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors

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