Thiazolides as novel antiviral agents. 2. Inhibition of hepatitis C virus replication.
Identifieur interne : 001410 ( PubMed/Checkpoint ); précédent : 001409; suivant : 001411Thiazolides as novel antiviral agents. 2. Inhibition of hepatitis C virus replication.
Auteurs : Andrew V. Stachulski [Royaume-Uni] ; Chandrakala Pidathala ; Eleanor C. Row ; Raman Sharma ; Neil G. Berry ; Alexandre S. Lawrenson ; Shelley L. Moores ; Mazhar Iqbal ; Joanne Bentley ; Sarah A. Allman ; Geoffrey Edwards ; Alison Helm ; Jennifer Hellier ; Brent E. Korba ; J Edward Semple ; Jean-Francois RossignolSource :
- Journal of medicinal chemistry [ 1520-4804 ] ; 2011.
Descripteurs français
- KwdFr :
- Amides (), Amides (pharmacologie), Amides (synthèse chimique), Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Hepacivirus (), Hepacivirus (génétique), Hepacivirus (physiologie), Humains, Lignée cellulaire, Relation quantitative structure-activité, Réplication virale (), Thiazoles (), Thiazoles (pharmacologie), Thiazoles (synthèse chimique).
- MESH :
- génétique : Hepacivirus.
- pharmacologie : Amides, Antiviraux, Thiazoles.
- physiologie : Hepacivirus.
- synthèse chimique : Amides, Antiviraux, Thiazoles.
- Amides, Antiviraux, Hepacivirus, Humains, Lignée cellulaire, Relation quantitative structure-activité, Réplication virale, Thiazoles.
English descriptors
- KwdEn :
- Amides (chemical synthesis), Amides (chemistry), Amides (pharmacology), Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cell Line, Hepacivirus (drug effects), Hepacivirus (genetics), Hepacivirus (physiology), Humans, Quantitative Structure-Activity Relationship, Thiazoles (chemical synthesis), Thiazoles (chemistry), Thiazoles (pharmacology), Virus Replication (drug effects).
- MESH :
- chemical , chemical synthesis : Amides, Antiviral Agents, Thiazoles.
- chemical , chemistry : Amides, Antiviral Agents, Thiazoles.
- chemical , pharmacology : Amides, Antiviral Agents, Thiazoles.
- drug effects : Hepacivirus, Virus Replication.
- genetics : Hepacivirus.
- physiology : Hepacivirus.
- Cell Line, Humans, Quantitative Structure-Activity Relationship.
Abstract
We report the activities of a number of thiazolides [2-hydroxyaroyl-N-(thiazol-2-yl)amides] against hepatitis C virus (HCV) genotypes IA and IB, using replicon assays. The structure-activity relationships (SARs) of thiazolides against HCV are less predictable than against hepatitis B virus (HBV), though an electron-withdrawing group at C(5') generally correlates with potency. Among the related salicyloylanilides, the m-fluorophenyl analogue was most promising; niclosamide and close analogues suffered from very low solubility and bioavailability. Nitazoxanide (NTZ) 1 has performed well in clinical trials against HCV. We show here that the 5'-Cl analogue 4 has closely comparable in vitro activity and a good cell safety index. By use of support vector analysis, a quantitative structure-activity relationship (QSAR) model was obtained, showing good predictive models for cell safety. We conclude by updating the mode of action of the thiazolides and explain the candidate selection that has led to compound 4 entering preclinical development.
DOI: 10.1021/jm201264t
PubMed: 22059983
Affiliations:
Links toward previous steps (curation, corpus...)
Links to Exploration step
pubmed:22059983Le document en format XML
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<front><div type="abstract" xml:lang="en">We report the activities of a number of thiazolides [2-hydroxyaroyl-N-(thiazol-2-yl)amides] against hepatitis C virus (HCV) genotypes IA and IB, using replicon assays. The structure-activity relationships (SARs) of thiazolides against HCV are less predictable than against hepatitis B virus (HBV), though an electron-withdrawing group at C(5') generally correlates with potency. Among the related salicyloylanilides, the m-fluorophenyl analogue was most promising; niclosamide and close analogues suffered from very low solubility and bioavailability. Nitazoxanide (NTZ) 1 has performed well in clinical trials against HCV. We show here that the 5'-Cl analogue 4 has closely comparable in vitro activity and a good cell safety index. By use of support vector analysis, a quantitative structure-activity relationship (QSAR) model was obtained, showing good predictive models for cell safety. We conclude by updating the mode of action of the thiazolides and explain the candidate selection that has led to compound 4 entering preclinical development.</div>
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<Abstract><AbstractText>We report the activities of a number of thiazolides [2-hydroxyaroyl-N-(thiazol-2-yl)amides] against hepatitis C virus (HCV) genotypes IA and IB, using replicon assays. The structure-activity relationships (SARs) of thiazolides against HCV are less predictable than against hepatitis B virus (HBV), though an electron-withdrawing group at C(5') generally correlates with potency. Among the related salicyloylanilides, the m-fluorophenyl analogue was most promising; niclosamide and close analogues suffered from very low solubility and bioavailability. Nitazoxanide (NTZ) 1 has performed well in clinical trials against HCV. We show here that the 5'-Cl analogue 4 has closely comparable in vitro activity and a good cell safety index. By use of support vector analysis, a quantitative structure-activity relationship (QSAR) model was obtained, showing good predictive models for cell safety. We conclude by updating the mode of action of the thiazolides and explain the candidate selection that has led to compound 4 entering preclinical development.</AbstractText>
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<name sortKey="Iqbal, Mazhar" sort="Iqbal, Mazhar" uniqKey="Iqbal M" first="Mazhar" last="Iqbal">Mazhar Iqbal</name>
<name sortKey="Korba, Brent E" sort="Korba, Brent E" uniqKey="Korba B" first="Brent E" last="Korba">Brent E. Korba</name>
<name sortKey="Lawrenson, Alexandre S" sort="Lawrenson, Alexandre S" uniqKey="Lawrenson A" first="Alexandre S" last="Lawrenson">Alexandre S. Lawrenson</name>
<name sortKey="Moores, Shelley L" sort="Moores, Shelley L" uniqKey="Moores S" first="Shelley L" last="Moores">Shelley L. Moores</name>
<name sortKey="Pidathala, Chandrakala" sort="Pidathala, Chandrakala" uniqKey="Pidathala C" first="Chandrakala" last="Pidathala">Chandrakala Pidathala</name>
<name sortKey="Rossignol, Jean Francois" sort="Rossignol, Jean Francois" uniqKey="Rossignol J" first="Jean-Francois" last="Rossignol">Jean-Francois Rossignol</name>
<name sortKey="Row, Eleanor C" sort="Row, Eleanor C" uniqKey="Row E" first="Eleanor C" last="Row">Eleanor C. Row</name>
<name sortKey="Semple, J Edward" sort="Semple, J Edward" uniqKey="Semple J" first="J Edward" last="Semple">J Edward Semple</name>
<name sortKey="Sharma, Raman" sort="Sharma, Raman" uniqKey="Sharma R" first="Raman" last="Sharma">Raman Sharma</name>
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<country name="Royaume-Uni"><noRegion><name sortKey="Stachulski, Andrew V" sort="Stachulski, Andrew V" uniqKey="Stachulski A" first="Andrew V" last="Stachulski">Andrew V. Stachulski</name>
</noRegion>
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