Novel 3-sulphonamido-quinazolin-4(3H)-one derivatives : microwave-assisted synthesis and evaluation of antiviral activities against respiratory and biodefense viruses
Identifieur interne : 000F26 ( Main/Exploration ); précédent : 000F25; suivant : 000F27Novel 3-sulphonamido-quinazolin-4(3H)-one derivatives : microwave-assisted synthesis and evaluation of antiviral activities against respiratory and biodefense viruses
Auteurs : Periyasamy Selvam [Inde] ; Paulchamy Vijayalakshimi [Inde] ; Donald F. Smee [États-Unis] ; Brian B. Gowen [États-Unis] ; Justin G. Julander [États-Unis] ; Craig W. Day [États-Unis] ; Dale L. Barnard [États-Unis]Source :
- Antiviral chemistry & chemotherapy [ 0956-3202 ] ; 2007.
Descripteurs français
- Pascal (Inist)
English descriptors
- KwdEn :
Abstract
We designed and synthesized novel 2,3-disubstituted quinazolin-4(3H)-ones by microwave technique and characterized them by spectral analysis. Synthesized compounds were screened for cytotoxicity and for antiviral activity against influenza A (H1N1, H3N2 and H5N1), severe acute respiratory syndrome corona, dengue, yellow fever, Venezuelan equine encephalitis (VEE), Rift Valley fever, and Tacaribe viruses in cell culture. A neutral red uptake assay was used to determine 50% virus-inhibitory concentrations (EC50) of test compounds and their 50% cytotoxicity concentration (CC50) in uninfected Madin-Darby canine kidney, Vero, and Vero 76 cells; selectivity indices (ratio of CC50 to EC50) were derived from the data. The compound 4-(6,8-dibromo-4-oxo-2-phenyl quinazolin-3(4H)-yl)-N-(4,5-dimethyloxazol-2yl) benzenesulphonamide 15 inhibited the replication of avian influenza (H5N1) virus (EC50=8.4 ug/ml, CC50>100 μg/ml, Sl>11.9) as did 4-(6-bromo-4oxo-2phenylquinazolin-3(4H)-yl) benzene]sulphonamide 5 (EC50=3 (μg/ml, CC50= 32 μg/ml, Sl=11). Compound 5 was also moderately active against VEE and Tacaribe viruses. The methodology described in this report is applicable for rapid synthesis of many compounds with potential antiviral properties.
Affiliations:
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Le document en format XML
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<series><title level="j" type="main">Antiviral chemistry & chemotherapy</title>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term>
<term>Chemical synthesis</term>
<term>Evaluation</term>
<term>Influenzavirus A(H5N1)</term>
<term>Respiratory tract</term>
<term>Tacaribe virus</term>
<term>Venezuelan equine encephalomyelitis virus</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Virus encéphalite équine Venezuela</term>
<term>Evaluation</term>
<term>Antiviral</term>
<term>Voie respiratoire</term>
<term>Synthèse chimique</term>
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<term>Dérivé de la quinazolinone</term>
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<front><div type="abstract" xml:lang="en">We designed and synthesized novel 2,3-disubstituted quinazolin-4(3H)-ones by microwave technique and characterized them by spectral analysis. Synthesized compounds were screened for cytotoxicity and for antiviral activity against influenza A (H1N1, H3N2 and H5N1), severe acute respiratory syndrome corona, dengue, yellow fever, Venezuelan equine encephalitis (VEE), Rift Valley fever, and Tacaribe viruses in cell culture. A neutral red uptake assay was used to determine 50% virus-inhibitory concentrations (EC<sub>50</sub>
) of test compounds and their 50% cytotoxicity concentration (CC<sub>50</sub>
) in uninfected Madin-Darby canine kidney, Vero, and Vero 76 cells; selectivity indices (ratio of CC<sub>50</sub>
to EC<sub>50</sub>
) were derived from the data. The compound 4-(6,8-dibromo-4-oxo-2-phenyl quinazolin-3(4H)-yl)-N-(4,5-dimethyloxazol-2yl) benzenesulphonamide 15 inhibited the replication of avian influenza (H5N1) virus (EC<sub>50</sub>
=8.4 ug/ml, CC<sub>50</sub>
>100 μg/ml, Sl>11.9) as did 4-(6-bromo-4oxo-2phenylquinazolin-3(4H)-yl) benzene]sulphonamide 5 (EC<sub>50</sub>
=3 (μg/ml, CC<sub>50</sub>
= 32 μg/ml, Sl=11). Compound 5 was also moderately active against VEE and Tacaribe viruses. The methodology described in this report is applicable for rapid synthesis of many compounds with potential antiviral properties.</div>
</front>
</TEI>
<affiliations><list><country><li>Inde</li>
<li>États-Unis</li>
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<region><li>Utah</li>
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<tree><country name="Inde"><noRegion><name sortKey="Selvam, Periyasamy" sort="Selvam, Periyasamy" uniqKey="Selvam P" first="Periyasamy" last="Selvam">Periyasamy Selvam</name>
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<name sortKey="Vijayalakshimi, Paulchamy" sort="Vijayalakshimi, Paulchamy" uniqKey="Vijayalakshimi P" first="Paulchamy" last="Vijayalakshimi">Paulchamy Vijayalakshimi</name>
</country>
<country name="États-Unis"><region name="Utah"><name sortKey="Smee, Donald F" sort="Smee, Donald F" uniqKey="Smee D" first="Donald F." last="Smee">Donald F. Smee</name>
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<name sortKey="Barnard, Dale L" sort="Barnard, Dale L" uniqKey="Barnard D" first="Dale L." last="Barnard">Dale L. Barnard</name>
<name sortKey="Day, Craig W" sort="Day, Craig W" uniqKey="Day C" first="Craig W." last="Day">Craig W. Day</name>
<name sortKey="Gowen, Brian B" sort="Gowen, Brian B" uniqKey="Gowen B" first="Brian B." last="Gowen">Brian B. Gowen</name>
<name sortKey="Julander, Justin G" sort="Julander, Justin G" uniqKey="Julander J" first="Justin G." last="Julander">Justin G. Julander</name>
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