Arylazolyl(azinyl)thioacetanilides. Part 20: Discovery of novel purinylthioacetanilides derivatives as potent HIV-1 NNRTIs via a structure-based bioisosterism approach.
Identifieur interne : 001077 ( Main/Exploration ); précédent : 001076; suivant : 001078Arylazolyl(azinyl)thioacetanilides. Part 20: Discovery of novel purinylthioacetanilides derivatives as potent HIV-1 NNRTIs via a structure-based bioisosterism approach.
Auteurs : Xueyi Lu [République populaire de Chine] ; Xiao Li [République populaire de Chine] ; Jiapei Yang [République populaire de Chine] ; Boshi Huang [République populaire de Chine] ; Dongwei Kang [République populaire de Chine] ; Fabao Zhao [République populaire de Chine] ; Zhongxia Zhou [République populaire de Chine] ; Erik De Clercq [Belgique] ; Dirk Daelemans [Belgique] ; Christophe Pannecouque [Belgique] ; Peng Zhan [République populaire de Chine] ; Xinyong Liu [République populaire de Chine]Source :
- Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2016.
Descripteurs français
- KwdFr :
- Acétanilides (), Acétanilides (pharmacologie), Agents antiVIH (), Agents antiVIH (pharmacologie), Inhibiteurs de la transcriptase inverse (), Inhibiteurs de la transcriptase inverse (pharmacologie), Modèles moléculaires, Relation structure-activité, Spectrométrie de masse ESI, Spectroscopie par résonance magnétique du carbone-13, Spectroscopie par résonance magnétique du proton, VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ().
- MESH :
- pharmacologie : Acétanilides, Agents antiVIH, Inhibiteurs de la transcriptase inverse.
- Acétanilides, Agents antiVIH, Inhibiteurs de la transcriptase inverse, Modèles moléculaires, Relation structure-activité, Spectrométrie de masse ESI, Spectroscopie par résonance magnétique du carbone-13, Spectroscopie par résonance magnétique du proton, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
English descriptors
- KwdEn :
- Acetanilides (chemistry), Acetanilides (pharmacology), Anti-HIV Agents (chemistry), Anti-HIV Agents (pharmacology), Carbon-13 Magnetic Resonance Spectroscopy, HIV-1 (drug effects), Models, Molecular, Proton Magnetic Resonance Spectroscopy, Reverse Transcriptase Inhibitors (chemistry), Reverse Transcriptase Inhibitors (pharmacology), Spectrometry, Mass, Electrospray Ionization, Structure-Activity Relationship.
- MESH :
- chemical , chemistry : Acetanilides, Anti-HIV Agents, Reverse Transcriptase Inhibitors.
- chemical , pharmacology : Acetanilides, Anti-HIV Agents, Reverse Transcriptase Inhibitors.
- drug effects : HIV-1.
- Carbon-13 Magnetic Resonance Spectroscopy, Models, Molecular, Proton Magnetic Resonance Spectroscopy, Spectrometry, Mass, Electrospray Ionization, Structure-Activity Relationship.
Abstract
By means of structure-based bioisosterism approach, a series of novel purinylthioacetanilide derivatives were designed, synthesized and evaluated as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Some of the tested compounds were found to be active against wild-type (WT) HIV-1(IIIB) with EC50 in the range of 0.78-4.46μM. Among them, LAD-8 displayed the most potent anti-HIV activity (EC50=0.78μM, SI=24). In addition, LBD-6 showed moderate activity against L100I mutant (EC50=5.64μM) and double mutant strain RES056 (EC50=22.24μM). Preliminary structure-activity relationships (SARs) were discussed in detail. Molecular modeling study was used to predict the optimal conformation in the NNRTI binding site, which may play a guiding role in further rational optimization.
DOI: 10.1016/j.bmc.2016.07.041
PubMed: 27501911
Affiliations:
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Le document en format XML
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<author><name sortKey="Kang, Dongwei" sort="Kang, Dongwei" uniqKey="Kang D" first="Dongwei" last="Kang">Dongwei Kang</name>
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<author><name sortKey="Zhao, Fabao" sort="Zhao, Fabao" uniqKey="Zhao F" first="Fabao" last="Zhao">Fabao Zhao</name>
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<author><name sortKey="Zhou, Zhongxia" sort="Zhou, Zhongxia" uniqKey="Zhou Z" first="Zhongxia" last="Zhou">Zhongxia Zhou</name>
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<author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name>
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<author><name sortKey="Zhan, Peng" sort="Zhan, Peng" uniqKey="Zhan P" first="Peng" last="Zhan">Peng Zhan</name>
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<author><name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name>
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<term>Acetanilides (pharmacology)</term>
<term>Anti-HIV Agents (chemistry)</term>
<term>Anti-HIV Agents (pharmacology)</term>
<term>Carbon-13 Magnetic Resonance Spectroscopy</term>
<term>HIV-1 (drug effects)</term>
<term>Models, Molecular</term>
<term>Proton Magnetic Resonance Spectroscopy</term>
<term>Reverse Transcriptase Inhibitors (chemistry)</term>
<term>Reverse Transcriptase Inhibitors (pharmacology)</term>
<term>Spectrometry, Mass, Electrospray Ionization</term>
<term>Structure-Activity Relationship</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Acétanilides ()</term>
<term>Acétanilides (pharmacologie)</term>
<term>Agents antiVIH ()</term>
<term>Agents antiVIH (pharmacologie)</term>
<term>Inhibiteurs de la transcriptase inverse ()</term>
<term>Inhibiteurs de la transcriptase inverse (pharmacologie)</term>
<term>Modèles moléculaires</term>
<term>Relation structure-activité</term>
<term>Spectrométrie de masse ESI</term>
<term>Spectroscopie par résonance magnétique du carbone-13</term>
<term>Spectroscopie par résonance magnétique du proton</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Acetanilides</term>
<term>Anti-HIV Agents</term>
<term>Reverse Transcriptase Inhibitors</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Acetanilides</term>
<term>Anti-HIV Agents</term>
<term>Reverse Transcriptase Inhibitors</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Acétanilides</term>
<term>Agents antiVIH</term>
<term>Inhibiteurs de la transcriptase inverse</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Carbon-13 Magnetic Resonance Spectroscopy</term>
<term>Models, Molecular</term>
<term>Proton Magnetic Resonance Spectroscopy</term>
<term>Spectrometry, Mass, Electrospray Ionization</term>
<term>Structure-Activity Relationship</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Acétanilides</term>
<term>Agents antiVIH</term>
<term>Inhibiteurs de la transcriptase inverse</term>
<term>Modèles moléculaires</term>
<term>Relation structure-activité</term>
<term>Spectrométrie de masse ESI</term>
<term>Spectroscopie par résonance magnétique du carbone-13</term>
<term>Spectroscopie par résonance magnétique du proton</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term>
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</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">By means of structure-based bioisosterism approach, a series of novel purinylthioacetanilide derivatives were designed, synthesized and evaluated as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Some of the tested compounds were found to be active against wild-type (WT) HIV-1(IIIB) with EC50 in the range of 0.78-4.46μM. Among them, LAD-8 displayed the most potent anti-HIV activity (EC50=0.78μM, SI=24). In addition, LBD-6 showed moderate activity against L100I mutant (EC50=5.64μM) and double mutant strain RES056 (EC50=22.24μM). Preliminary structure-activity relationships (SARs) were discussed in detail. Molecular modeling study was used to predict the optimal conformation in the NNRTI binding site, which may play a guiding role in further rational optimization.</div>
</front>
</TEI>
<affiliations><list><country><li>Belgique</li>
<li>République populaire de Chine</li>
</country>
</list>
<tree><country name="République populaire de Chine"><noRegion><name sortKey="Lu, Xueyi" sort="Lu, Xueyi" uniqKey="Lu X" first="Xueyi" last="Lu">Xueyi Lu</name>
</noRegion>
<name sortKey="Huang, Boshi" sort="Huang, Boshi" uniqKey="Huang B" first="Boshi" last="Huang">Boshi Huang</name>
<name sortKey="Kang, Dongwei" sort="Kang, Dongwei" uniqKey="Kang D" first="Dongwei" last="Kang">Dongwei Kang</name>
<name sortKey="Li, Xiao" sort="Li, Xiao" uniqKey="Li X" first="Xiao" last="Li">Xiao Li</name>
<name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name>
<name sortKey="Yang, Jiapei" sort="Yang, Jiapei" uniqKey="Yang J" first="Jiapei" last="Yang">Jiapei Yang</name>
<name sortKey="Zhan, Peng" sort="Zhan, Peng" uniqKey="Zhan P" first="Peng" last="Zhan">Peng Zhan</name>
<name sortKey="Zhao, Fabao" sort="Zhao, Fabao" uniqKey="Zhao F" first="Fabao" last="Zhao">Fabao Zhao</name>
<name sortKey="Zhou, Zhongxia" sort="Zhou, Zhongxia" uniqKey="Zhou Z" first="Zhongxia" last="Zhou">Zhongxia Zhou</name>
</country>
<country name="Belgique"><noRegion><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name>
</noRegion>
<name sortKey="Daelemans, Dirk" sort="Daelemans, Dirk" uniqKey="Daelemans D" first="Dirk" last="Daelemans">Dirk Daelemans</name>
<name sortKey="Pannecouque, Christophe" sort="Pannecouque, Christophe" uniqKey="Pannecouque C" first="Christophe" last="Pannecouque">Christophe Pannecouque</name>
</country>
</tree>
</affiliations>
</record>
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