Synthesis and anti-HIV activity of 4-(naphthalen-1-yl)-1,2,5-thiadiazol-3-hydroxyl derivatives.
Identifieur interne : 001559 ( Main/Exploration ); précédent : 001558; suivant : 001560Synthesis and anti-HIV activity of 4-(naphthalen-1-yl)-1,2,5-thiadiazol-3-hydroxyl derivatives.
Auteurs : Diwakar Rai [République populaire de Chine] ; Wenmin Chen ; Peng Zhan ; Hong Liu ; Ye Tian ; Xin Liang ; Erik De Clercq ; Christophe Pannecouque ; Jan Balzarini ; Xinyong LiuSource :
- Chemical biology & drug design [ 1747-0285 ] ; 2014.
Descripteurs français
- KwdFr :
- Humains, Inhibiteurs de la transcriptase inverse (), Inhibiteurs de la transcriptase inverse (pharmacologie), Inhibiteurs de la transcriptase inverse (synthèse chimique), Lignée cellulaire, Naphtalènes (), Relation structure-activité, Régulation allostérique, Réplication virale (), Simulation de docking moléculaire, Sites de fixation, Structure tertiaire des protéines, Thiadiazoles (), Thiadiazoles (pharmacologie), Thiadiazoles (synthèse chimique), Transcriptase inverse du VIH (antagonistes et inhibiteurs), Transcriptase inverse du VIH (métabolisme), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (enzymologie).
- MESH :
- antagonistes et inhibiteurs : Transcriptase inverse du VIH.
- enzymologie : VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
- métabolisme : Transcriptase inverse du VIH.
- pharmacologie : Inhibiteurs de la transcriptase inverse, Thiadiazoles.
- synthèse chimique : Inhibiteurs de la transcriptase inverse, Thiadiazoles.
- Humains, Inhibiteurs de la transcriptase inverse, Lignée cellulaire, Naphtalènes, Relation structure-activité, Régulation allostérique, Réplication virale, Simulation de docking moléculaire, Sites de fixation, Structure tertiaire des protéines, Thiadiazoles.
English descriptors
- KwdEn :
- Allosteric Regulation, Binding Sites, Cell Line, HIV Reverse Transcriptase (antagonists & inhibitors), HIV Reverse Transcriptase (metabolism), HIV-1 (enzymology), Humans, Molecular Docking Simulation, Naphthalenes (chemistry), Protein Structure, Tertiary, Reverse Transcriptase Inhibitors (chemical synthesis), Reverse Transcriptase Inhibitors (chemistry), Reverse Transcriptase Inhibitors (pharmacology), Structure-Activity Relationship, Thiadiazoles (chemical synthesis), Thiadiazoles (chemistry), Thiadiazoles (pharmacology), Virus Replication (drug effects).
- MESH :
- chemical , antagonists & inhibitors : HIV Reverse Transcriptase.
- chemical , chemical synthesis : Reverse Transcriptase Inhibitors, Thiadiazoles.
- chemical , chemistry : Naphthalenes, Reverse Transcriptase Inhibitors, Thiadiazoles.
- chemical , metabolism : HIV Reverse Transcriptase.
- drug effects : Virus Replication.
- enzymology : HIV-1.
- chemical , pharmacology : Reverse Transcriptase Inhibitors, Thiadiazoles.
- Allosteric Regulation, Binding Sites, Cell Line, Humans, Molecular Docking Simulation, Protein Structure, Tertiary, Structure-Activity Relationship.
Abstract
A series of 4-(naphthalen-1-yl)-1,2,5-thiadiazol-3-hydroxyl derivatives (Ia-Im and IIa-IIe) designed as novel HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) was synthesized via an expeditious route and evaluated for their anti-HIV activities in MT-4 cell cultures. All the synthesized compounds were structurally confirmed by spectral analyses. Biological results showed that three analogues displayed moderate inhibitory activity against wild-type (wt) HIV-1 replication with EC(50) values ranging from 16 to 22 μm. Molecular docking of compound Ih with wt HIV-1 RT was performed to understand the binding mode between these inhibitors and the wt HIV-1 RT and to rationalize some SARs.
DOI: 10.1111/cbdd.12328
PubMed: 24674646
Affiliations:
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250012</wicri:regionArea><wicri:noRegion>250012</wicri:noRegion></affiliation></author><author><name sortKey="Chen, Wenmin" sort="Chen, Wenmin" uniqKey="Chen W" first="Wenmin" last="Chen">Wenmin Chen</name></author><author><name sortKey="Zhan, Peng" sort="Zhan, Peng" uniqKey="Zhan P" first="Peng" last="Zhan">Peng Zhan</name></author><author><name sortKey="Liu, Hong" sort="Liu, Hong" uniqKey="Liu H" first="Hong" last="Liu">Hong Liu</name></author><author><name sortKey="Tian, Ye" sort="Tian, Ye" uniqKey="Tian Y" first="Ye" last="Tian">Ye Tian</name></author><author><name sortKey="Liang, Xin" sort="Liang, Xin" uniqKey="Liang X" first="Xin" last="Liang">Xin Liang</name></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name></author><author><name sortKey="Pannecouque, Christophe" sort="Pannecouque, Christophe" uniqKey="Pannecouque C" first="Christophe" last="Pannecouque">Christophe Pannecouque</name></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name></author><author><name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name></author></analytic><series><title level="j">Chemical biology & drug design</title><idno type="eISSN">1747-0285</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Allosteric Regulation</term><term>Binding Sites</term><term>Cell Line</term><term>HIV Reverse Transcriptase (antagonists & inhibitors)</term><term>HIV Reverse Transcriptase (metabolism)</term><term>HIV-1 (enzymology)</term><term>Humans</term><term>Molecular Docking Simulation</term><term>Naphthalenes (chemistry)</term><term>Protein Structure, Tertiary</term><term>Reverse Transcriptase Inhibitors (chemical synthesis)</term><term>Reverse Transcriptase Inhibitors (chemistry)</term><term>Reverse Transcriptase Inhibitors (pharmacology)</term><term>Structure-Activity Relationship</term><term>Thiadiazoles (chemical synthesis)</term><term>Thiadiazoles (chemistry)</term><term>Thiadiazoles (pharmacology)</term><term>Virus Replication (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Humains</term><term>Inhibiteurs de la transcriptase inverse ()</term><term>Inhibiteurs de la transcriptase inverse (pharmacologie)</term><term>Inhibiteurs de la transcriptase inverse (synthèse chimique)</term><term>Lignée cellulaire</term><term>Naphtalènes ()</term><term>Relation structure-activité</term><term>Régulation allostérique</term><term>Réplication virale ()</term><term>Simulation de docking moléculaire</term><term>Sites de fixation</term><term>Structure tertiaire des protéines</term><term>Thiadiazoles ()</term><term>Thiadiazoles (pharmacologie)</term><term>Thiadiazoles (synthèse chimique)</term><term>Transcriptase inverse du VIH (antagonistes et inhibiteurs)</term><term>Transcriptase inverse du VIH (métabolisme)</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (enzymologie)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>HIV Reverse Transcriptase</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Reverse Transcriptase Inhibitors</term><term>Thiadiazoles</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Naphthalenes</term><term>Reverse Transcriptase Inhibitors</term><term>Thiadiazoles</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>HIV Reverse Transcriptase</term></keywords><keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Transcriptase inverse du VIH</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Virus Replication</term></keywords><keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>HIV-1</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Transcriptase inverse du VIH</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Inhibiteurs de la transcriptase inverse</term><term>Thiadiazoles</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Reverse Transcriptase Inhibitors</term><term>Thiadiazoles</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Inhibiteurs de la transcriptase inverse</term><term>Thiadiazoles</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Allosteric Regulation</term><term>Binding Sites</term><term>Cell Line</term><term>Humans</term><term>Molecular Docking Simulation</term><term>Protein Structure, Tertiary</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Humains</term><term>Inhibiteurs de la transcriptase inverse</term><term>Lignée cellulaire</term><term>Naphtalènes</term><term>Relation structure-activité</term><term>Régulation allostérique</term><term>Réplication virale</term><term>Simulation de docking moléculaire</term><term>Sites de fixation</term><term>Structure tertiaire des protéines</term><term>Thiadiazoles</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A series of 4-(naphthalen-1-yl)-1,2,5-thiadiazol-3-hydroxyl derivatives (Ia-Im and IIa-IIe) designed as novel HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) was synthesized via an expeditious route and evaluated for their anti-HIV activities in MT-4 cell cultures. All the synthesized compounds were structurally confirmed by spectral analyses. Biological results showed that three analogues displayed moderate inhibitory activity against wild-type (wt) HIV-1 replication with EC(50) values ranging from 16 to 22 μm. Molecular docking of compound Ih with wt HIV-1 RT was performed to understand the binding mode between these inhibitors and the wt HIV-1 RT and to rationalize some SARs.</div></front></TEI><affiliations><list><country><li>République populaire de Chine</li></country></list><tree><noCountry><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><name sortKey="Chen, Wenmin" sort="Chen, Wenmin" uniqKey="Chen W" first="Wenmin" last="Chen">Wenmin Chen</name><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><name sortKey="Liang, Xin" sort="Liang, Xin" uniqKey="Liang X" first="Xin" last="Liang">Xin Liang</name><name sortKey="Liu, Hong" sort="Liu, Hong" uniqKey="Liu H" first="Hong" last="Liu">Hong Liu</name><name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name><name sortKey="Pannecouque, Christophe" sort="Pannecouque, Christophe" uniqKey="Pannecouque C" first="Christophe" last="Pannecouque">Christophe Pannecouque</name><name sortKey="Tian, Ye" sort="Tian, Ye" uniqKey="Tian Y" first="Ye" last="Tian">Ye Tian</name><name sortKey="Zhan, Peng" sort="Zhan, Peng" uniqKey="Zhan P" first="Peng" last="Zhan">Peng Zhan</name></noCountry><country name="République populaire de Chine"><noRegion><name sortKey="Rai, Diwakar" sort="Rai, Diwakar" uniqKey="Rai D" first="Diwakar" last="Rai">Diwakar Rai</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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