Design and efficient synthesis of novel arylthiourea derivatives as potent hepatitis C virus inhibitors
Identifieur interne : 000221 ( PascalFrancis/Checkpoint ); précédent : 000220; suivant : 000222Design and efficient synthesis of novel arylthiourea derivatives as potent hepatitis C virus inhibitors
Auteurs : Iou-Jiun Kang [Taïwan] ; Li-Wen Wang [Taïwan] ; Sheng-Ju Hsu [Taïwan] ; Chung-Chi Lee [Taïwan] ; Yen-Chun Lee [Taïwan] ; Yen-Shian Wu [Taïwan] ; Andrew Yueh [Taïwan] ; Jing-Chyi Wang [Taïwan] ; Tsu-An Hsu [Taïwan] ; Yu-Sheng Chao [Taïwan] ; Jyh-Haur Chern [Taïwan]Source :
- Bioorganic & medicinal chemistry letters : (Print) [ 0960-894X ] ; 2009.
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Abstract
A novel class of arylthiourea HCV inhibitors bearing various functionalities, such as cyclic urea, cyclic thiourea, urea, and thiourea, on the alkyl linker were designed and synthesized. Herein we report the synthesis and structure-activity relationships (SARs) of this novel class of arylthiourea derivatives that showed potent inhibitory activities against HCV in the cell-based subgenomic HCV replicon assay. Among compounds tested, the new carbazole derivative 64, which has an eight-carbon linkage between the phenyl and carbazole rings and a tolyl group at the N-9 position of carbazole, was found to possess strong anti-HCV activity (EC50=0.031 μM), lower cytotoxicity (CC50 >50 μM), and higher selectivity index (SI >1612) compared to its derivatives.
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en" level="a">Design and efficient synthesis of novel arylthiourea derivatives as potent hepatitis C virus inhibitors</title><author><name sortKey="Kang, Iou Jiun" sort="Kang, Iou Jiun" uniqKey="Kang I" first="Iou-Jiun" last="Kang">Iou-Jiun Kang</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Wang, Li Wen" sort="Wang, Li Wen" uniqKey="Wang L" first="Li-Wen" last="Wang">Li-Wen Wang</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Hsu, Sheng Ju" sort="Hsu, Sheng Ju" uniqKey="Hsu S" first="Sheng-Ju" last="Hsu">Sheng-Ju Hsu</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Lee, Chung Chi" sort="Lee, Chung Chi" uniqKey="Lee C" first="Chung-Chi" last="Lee">Chung-Chi Lee</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Lee, Yen Chun" sort="Lee, Yen Chun" uniqKey="Lee Y" first="Yen-Chun" last="Lee">Yen-Chun Lee</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, 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aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">INIST</idno><idno type="inist">10-0093032</idno><date when="2009">2009</date><idno type="stanalyst">PASCAL 10-0093032 INIST</idno><idno type="RBID">Pascal:10-0093032</idno><idno type="wicri:Area/PascalFrancis/Corpus">000172</idno><idno type="wicri:Area/PascalFrancis/Curation">000816</idno><idno type="wicri:Area/PascalFrancis/Checkpoint">000221</idno><idno type="wicri:explorRef" wicri:stream="PascalFrancis" wicri:step="Checkpoint">000221</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">Design and efficient synthesis of novel arylthiourea derivatives as potent hepatitis C virus inhibitors</title><author><name sortKey="Kang, Iou Jiun" sort="Kang, Iou Jiun" uniqKey="Kang I" first="Iou-Jiun" last="Kang">Iou-Jiun Kang</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Wang, Li Wen" sort="Wang, Li Wen" uniqKey="Wang L" first="Li-Wen" last="Wang">Li-Wen Wang</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Hsu, Sheng Ju" sort="Hsu, Sheng Ju" uniqKey="Hsu S" first="Sheng-Ju" last="Hsu">Sheng-Ju Hsu</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Lee, Chung Chi" sort="Lee, Chung Chi" uniqKey="Lee C" first="Chung-Chi" last="Lee">Chung-Chi Lee</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Lee, Yen Chun" sort="Lee, Yen Chun" uniqKey="Lee Y" first="Yen-Chun" last="Lee">Yen-Chun Lee</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Wu, Yen Shian" sort="Wu, Yen Shian" uniqKey="Wu Y" first="Yen-Shian" last="Wu">Yen-Shian Wu</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Yueh, Andrew" sort="Yueh, Andrew" uniqKey="Yueh A" first="Andrew" last="Yueh">Andrew Yueh</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Wang, Jing Chyi" sort="Wang, Jing Chyi" uniqKey="Wang J" first="Jing-Chyi" last="Wang">Jing-Chyi Wang</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Hsu, Tsu An" sort="Hsu, Tsu An" uniqKey="Hsu T" first="Tsu-An" last="Hsu">Tsu-An Hsu</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Chao, Yu Sheng" sort="Chao, Yu Sheng" uniqKey="Chao Y" first="Yu-Sheng" last="Chao">Yu-Sheng Chao</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author><author><name sortKey="Chern, Jyh Haur" sort="Chern, Jyh Haur" uniqKey="Chern J" first="Jyh-Haur" last="Chern">Jyh-Haur Chern</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></inist:fA14><country>Taïwan</country><wicri:noRegion>Zhunan Town, Miaoli County 350</wicri:noRegion></affiliation></author></analytic><series><title level="j" type="main">Bioorganic & medicinal chemistry letters : (Print)</title><title level="j" type="abbreviated">Bioorg. med. chem. lett. : (Print)</title><idno type="ISSN">0960-894X</idno><imprint><date when="2009">2009</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Bioorganic & medicinal chemistry letters : (Print)</title><title level="j" type="abbreviated">Bioorg. med. chem. lett. : (Print)</title><idno type="ISSN">0960-894X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aliphatic compound</term><term>Antiviral</term><term>Aromatic compound</term><term>Benzene derivatives</term><term>Carbazole derivatives</term><term>Chain length</term><term>Chemical synthesis</term><term>Ether</term><term>Hepatitis C virus</term><term>In vitro</term><term>Nitrogen heterocycle</term><term>Structure activity relation</term><term>Thioureas</term><term>Tricyclic compound</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Synthèse chimique</term><term>Thiourées</term><term>Antiviral</term><term>Virus hépatite C</term><term>Relation structure activité</term><term>Dérivé du benzène</term><term>Ether</term><term>Longueur chaîne</term><term>Dérivé du carbazole</term><term>Hétérocycle azote</term><term>Composé tricyclique</term><term>Composé aromatique</term><term>Composé aliphatique</term><term>In vitro</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A novel class of arylthiourea HCV inhibitors bearing various functionalities, such as cyclic urea, cyclic thiourea, urea, and thiourea, on the alkyl linker were designed and synthesized. Herein we report the synthesis and structure-activity relationships (SARs) of this novel class of arylthiourea derivatives that showed potent inhibitory activities against HCV in the cell-based subgenomic HCV replicon assay. Among compounds tested, the new carbazole derivative 64, which has an eight-carbon linkage between the phenyl and carbazole rings and a tolyl group at the N-9 position of carbazole, was found to possess strong anti-HCV activity (EC<sub>50</sub>=0.031 μM), lower cytotoxicity (CC<sub>50</sub> >50 μM), and higher selectivity index (SI >1612) compared to its derivatives.</div></front></TEI><inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>0960-894X</s0></fA01><fA03 i2="1"><s0>Bioorg. med. chem. lett. : (Print)</s0></fA03><fA05><s2>19</s2></fA05><fA06><s2>21</s2></fA06><fA08 i1="01" i2="1" l="ENG"><s1>Design and efficient synthesis of novel arylthiourea derivatives as potent hepatitis C virus inhibitors</s1></fA08><fA11 i1="01" i2="1"><s1>KANG (Iou-Jiun)</s1></fA11><fA11 i1="02" i2="1"><s1>WANG (Li-Wen)</s1></fA11><fA11 i1="03" i2="1"><s1>HSU (Sheng-Ju)</s1></fA11><fA11 i1="04" i2="1"><s1>LEE (Chung-Chi)</s1></fA11><fA11 i1="05" i2="1"><s1>LEE (Yen-Chun)</s1></fA11><fA11 i1="06" i2="1"><s1>WU (Yen-Shian)</s1></fA11><fA11 i1="07" i2="1"><s1>YUEH (Andrew)</s1></fA11><fA11 i1="08" i2="1"><s1>WANG (Jing-Chyi)</s1></fA11><fA11 i1="09" i2="1"><s1>HSU (Tsu-An)</s1></fA11><fA11 i1="10" i2="1"><s1>CHAO (Yu-Sheng)</s1></fA11><fA11 i1="11" i2="1"><s1>CHERN (Jyh-Haur)</s1></fA11><fA14 i1="01"><s1>Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, No. 35, Keyan Road</s1><s2>Zhunan Town, Miaoli County 350</s2><s3>TWN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ></fA14><fA20><s1>6063-6068</s1></fA20><fA21><s1>2009</s1></fA21><fA23 i1="01"><s0>ENG</s0></fA23><fA43 i1="01"><s1>INIST</s1><s2>22446</s2><s5>354000171259320160</s5></fA43><fA44><s0>0000</s0><s1>© 2010 INIST-CNRS. All rights reserved.</s1></fA44><fA45><s0>12 ref.</s0></fA45><fA47 i1="01" i2="1"><s0>10-0093032</s0></fA47><fA60><s1>P</s1></fA60><fA61><s0>A</s0></fA61><fA64 i1="01" i2="1"><s0>Bioorganic & medicinal chemistry letters : (Print)</s0></fA64><fA66 i1="01"><s0>GBR</s0></fA66><fC01 i1="01" l="ENG"><s0>A novel class of arylthiourea HCV inhibitors bearing various functionalities, such as cyclic urea, cyclic thiourea, urea, and thiourea, on the alkyl linker were designed and synthesized. Herein we report the synthesis and structure-activity relationships (SARs) of this novel class of arylthiourea derivatives that showed potent inhibitory activities against HCV in the cell-based subgenomic HCV replicon assay. Among compounds tested, the new carbazole derivative 64, which has an eight-carbon linkage between the phenyl and carbazole rings and a tolyl group at the N-9 position of carbazole, was found to possess strong anti-HCV activity (EC<sub>50</sub>=0.031 μM), lower cytotoxicity (CC<sub>50</sub> >50 μM), and higher selectivity index (SI >1612) compared to its derivatives.</s0></fC01><fC02 i1="01" i2="X"><s0>002B02S05</s0></fC02><fC03 i1="01" i2="X" l="FRE"><s0>Synthèse chimique</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="ENG"><s0>Chemical synthesis</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="SPA"><s0>Síntesis química</s0><s5>01</s5></fC03><fC03 i1="02" i2="X" l="FRE"><s0>Thiourées</s0><s5>02</s5></fC03><fC03 i1="02" i2="X" l="ENG"><s0>Thioureas</s0><s5>02</s5></fC03><fC03 i1="02" i2="X" l="SPA"><s0>Tioureas</s0><s5>02</s5></fC03><fC03 i1="03" i2="X" l="FRE"><s0>Antiviral</s0><s5>03</s5></fC03><fC03 i1="03" i2="X" l="ENG"><s0>Antiviral</s0><s5>03</s5></fC03><fC03 i1="03" i2="X" l="SPA"><s0>Antiviral</s0><s5>03</s5></fC03><fC03 i1="04" i2="X" l="FRE"><s0>Virus hépatite C</s0><s2>NW</s2><s5>04</s5></fC03><fC03 i1="04" i2="X" l="ENG"><s0>Hepatitis C virus</s0><s2>NW</s2><s5>04</s5></fC03><fC03 i1="04" i2="X" l="SPA"><s0>Hepatitis C virus</s0><s2>NW</s2><s5>04</s5></fC03><fC03 i1="05" i2="X" l="FRE"><s0>Relation structure activité</s0><s5>05</s5></fC03><fC03 i1="05" i2="X" l="ENG"><s0>Structure activity relation</s0><s5>05</s5></fC03><fC03 i1="05" i2="X" l="SPA"><s0>Relación estructura actividad</s0><s5>05</s5></fC03><fC03 i1="06" i2="X" l="FRE"><s0>Dérivé du benzène</s0><s5>06</s5></fC03><fC03 i1="06" i2="X" l="ENG"><s0>Benzene derivatives</s0><s5>06</s5></fC03><fC03 i1="06" i2="X" l="SPA"><s0>Benceno derivado</s0><s5>06</s5></fC03><fC03 i1="07" i2="X" l="FRE"><s0>Ether</s0><s2>FX</s2><s5>07</s5></fC03><fC03 i1="07" i2="X" l="ENG"><s0>Ether</s0><s2>FX</s2><s5>07</s5></fC03><fC03 i1="07" i2="X" l="SPA"><s0>Eter</s0><s2>FX</s2><s5>07</s5></fC03><fC03 i1="08" i2="X" l="FRE"><s0>Longueur chaîne</s0><s5>08</s5></fC03><fC03 i1="08" i2="X" l="ENG"><s0>Chain length</s0><s5>08</s5></fC03><fC03 i1="08" i2="X" l="SPA"><s0>Longitud cadena</s0><s5>08</s5></fC03><fC03 i1="09" i2="X" l="FRE"><s0>Dérivé du carbazole</s0><s5>09</s5></fC03><fC03 i1="09" i2="X" l="ENG"><s0>Carbazole derivatives</s0><s5>09</s5></fC03><fC03 i1="09" i2="X" l="SPA"><s0>Carbazol derivado</s0><s5>09</s5></fC03><fC03 i1="10" i2="X" l="FRE"><s0>Hétérocycle azote</s0><s5>10</s5></fC03><fC03 i1="10" i2="X" l="ENG"><s0>Nitrogen heterocycle</s0><s5>10</s5></fC03><fC03 i1="10" i2="X" l="SPA"><s0>Heterociclo nitrógeno</s0><s5>10</s5></fC03><fC03 i1="11" i2="X" l="FRE"><s0>Composé tricyclique</s0><s5>11</s5></fC03><fC03 i1="11" i2="X" l="ENG"><s0>Tricyclic compound</s0><s5>11</s5></fC03><fC03 i1="11" i2="X" l="SPA"><s0>Compuesto tricíclico</s0><s5>11</s5></fC03><fC03 i1="12" i2="X" l="FRE"><s0>Composé aromatique</s0><s5>12</s5></fC03><fC03 i1="12" i2="X" l="ENG"><s0>Aromatic compound</s0><s5>12</s5></fC03><fC03 i1="12" i2="X" l="SPA"><s0>Compuesto aromático</s0><s5>12</s5></fC03><fC03 i1="13" i2="X" l="FRE"><s0>Composé aliphatique</s0><s5>13</s5></fC03><fC03 i1="13" i2="X" l="ENG"><s0>Aliphatic compound</s0><s5>13</s5></fC03><fC03 i1="13" i2="X" l="SPA"><s0>Compuesto alifático</s0><s5>13</s5></fC03><fC03 i1="14" i2="X" l="FRE"><s0>In vitro</s0><s5>14</s5></fC03><fC03 i1="14" i2="X" l="ENG"><s0>In vitro</s0><s5>14</s5></fC03><fC03 i1="14" i2="X" l="SPA"><s0>In vitro</s0><s5>14</s5></fC03><fC07 i1="01" i2="X" l="FRE"><s0>Hepacivirus</s0><s2>NW</s2></fC07><fC07 i1="01" i2="X" l="ENG"><s0>Hepacivirus</s0><s2>NW</s2></fC07><fC07 i1="01" i2="X" l="SPA"><s0>Hepacivirus</s0><s2>NW</s2></fC07><fC07 i1="02" i2="X" l="FRE"><s0>Flaviviridae</s0><s2>NW</s2></fC07><fC07 i1="02" i2="X" l="ENG"><s0>Flaviviridae</s0><s2>NW</s2></fC07><fC07 i1="02" i2="X" l="SPA"><s0>Flaviviridae</s0><s2>NW</s2></fC07><fC07 i1="03" i2="X" l="FRE"><s0>Virus</s0><s2>NW</s2></fC07><fC07 i1="03" i2="X" l="ENG"><s0>Virus</s0><s2>NW</s2></fC07><fC07 i1="03" i2="X" l="SPA"><s0>Virus</s0><s2>NW</s2></fC07><fN21><s1>060</s1></fN21></pA></standard></inist><affiliations><list><country><li>Taïwan</li></country></list><tree><country name="Taïwan"><noRegion><name sortKey="Kang, Iou Jiun" sort="Kang, Iou Jiun" uniqKey="Kang I" first="Iou-Jiun" last="Kang">Iou-Jiun Kang</name></noRegion><name sortKey="Chao, Yu Sheng" sort="Chao, Yu Sheng" uniqKey="Chao Y" first="Yu-Sheng" last="Chao">Yu-Sheng Chao</name><name sortKey="Chern, Jyh Haur" sort="Chern, Jyh Haur" uniqKey="Chern J" first="Jyh-Haur" last="Chern">Jyh-Haur Chern</name><name sortKey="Hsu, Sheng Ju" sort="Hsu, Sheng Ju" uniqKey="Hsu S" first="Sheng-Ju" last="Hsu">Sheng-Ju Hsu</name><name sortKey="Hsu, Tsu An" sort="Hsu, Tsu An" uniqKey="Hsu T" first="Tsu-An" last="Hsu">Tsu-An Hsu</name><name sortKey="Lee, Chung Chi" sort="Lee, Chung Chi" uniqKey="Lee C" first="Chung-Chi" last="Lee">Chung-Chi Lee</name><name sortKey="Lee, Yen Chun" sort="Lee, Yen Chun" uniqKey="Lee Y" first="Yen-Chun" last="Lee">Yen-Chun Lee</name><name sortKey="Wang, Jing Chyi" sort="Wang, Jing Chyi" uniqKey="Wang J" first="Jing-Chyi" last="Wang">Jing-Chyi Wang</name><name sortKey="Wang, Li Wen" sort="Wang, Li Wen" uniqKey="Wang L" first="Li-Wen" last="Wang">Li-Wen Wang</name><name sortKey="Wu, Yen Shian" sort="Wu, Yen Shian" uniqKey="Wu Y" first="Yen-Shian" last="Wu">Yen-Shian Wu</name><name sortKey="Yueh, Andrew" sort="Yueh, Andrew" uniqKey="Yueh A" first="Andrew" last="Yueh">Andrew Yueh</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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