Synthesis and in vitro anti-HIV evaluation of a new series of 6-arylmethyl-substituted S-DABOs as potential non-nucleoside HIV-1 reverse transcriptase inhibitors.
Identifieur interne : 001D12 ( Ncbi/Merge ); précédent : 001D11; suivant : 001D13Synthesis and in vitro anti-HIV evaluation of a new series of 6-arylmethyl-substituted S-DABOs as potential non-nucleoside HIV-1 reverse transcriptase inhibitors.
Auteurs : Yue-Ping Wang [République populaire de Chine] ; Fen-Er Chen ; Erik De Clercq ; Jan Balzarini ; Christophe PannecouqueSource :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2009.
Descripteurs français
- KwdFr :
- Cristallographie aux rayons X, Humains, Inhibiteurs de la transcriptase inverse (), Inhibiteurs de la transcriptase inverse (pharmacologie), Inhibiteurs de la transcriptase inverse (synthèse chimique), Lignée cellulaire, Pyrimidinones (), Pyrimidinones (pharmacologie), Pyrimidinones (synthèse chimique), Relation structure-activité, Spectrométrie de masse ESI, Spectroscopie infrarouge à transformée de Fourier, Spectroscopie par résonance magnétique, Transcriptase inverse du VIH (antagonistes et inhibiteurs), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ().
- MESH :
- antagonistes et inhibiteurs : Transcriptase inverse du VIH.
- pharmacologie : Inhibiteurs de la transcriptase inverse, Pyrimidinones.
- synthèse chimique : Inhibiteurs de la transcriptase inverse, Pyrimidinones.
- Cristallographie aux rayons X, Humains, Inhibiteurs de la transcriptase inverse, Lignée cellulaire, Pyrimidinones, Relation structure-activité, Spectrométrie de masse ESI, Spectroscopie infrarouge à transformée de Fourier, Spectroscopie par résonance magnétique, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
English descriptors
- KwdEn :
- Cell Line, Crystallography, X-Ray, HIV Reverse Transcriptase (antagonists & inhibitors), HIV-1 (drug effects), Humans, Magnetic Resonance Spectroscopy, Pyrimidinones (chemical synthesis), Pyrimidinones (chemistry), Pyrimidinones (pharmacology), Reverse Transcriptase Inhibitors (chemical synthesis), Reverse Transcriptase Inhibitors (chemistry), Reverse Transcriptase Inhibitors (pharmacology), Spectrometry, Mass, Electrospray Ionization, Spectroscopy, Fourier Transform Infrared, Structure-Activity Relationship.
- MESH :
- chemical , antagonists & inhibitors : HIV Reverse Transcriptase.
- chemical , chemical synthesis : Pyrimidinones, Reverse Transcriptase Inhibitors.
- chemical , chemistry : Pyrimidinones, Reverse Transcriptase Inhibitors.
- drug effects : HIV-1.
- chemical , pharmacology : Pyrimidinones, Reverse Transcriptase Inhibitors.
- Cell Line, Crystallography, X-Ray, Humans, Magnetic Resonance Spectroscopy, Spectrometry, Mass, Electrospray Ionization, Spectroscopy, Fourier Transform Infrared, Structure-Activity Relationship.
Abstract
A series of new 5-alkyl-2-benzylsulfanylpyrimidin-4(3H)-ones (5a-y) bearing different substituted arylmethyl moieties at the C-6 position of the pyrimidine core have been synthesized and evaluated for their in vitro activities against HIV-1 and HIV-2 in MT-4 cell cultures. The majority of the title compounds showed moderate to good activities against HIV-1 with an IC(50) range from 6.67 microM to 0.12 microM. Among them, 6-(3,5-dimethylbenzyl) analogue 5q exhibited the most potent anti-HIV-1 activity (IC(50)=0.12 microM, SI>2642), which was about 40-fold more active than the reference compounds 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine (HEPT) and 2',3'-dideoxyinosine (DDI). The structure-activity relationships (SARs) of these new congeners were further discussed.
DOI: 10.1016/j.ejmech.2008.06.028
PubMed: 18692274
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pubmed:18692274Le document en format XML
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<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Fudan University, Shanghai 200433, PR China.</nlm:affiliation>
<country xml:lang="fr">République populaire de Chine</country>
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<author><name sortKey="Chen, Fen Er" sort="Chen, Fen Er" uniqKey="Chen F" first="Fen-Er" last="Chen">Fen-Er Chen</name>
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<term>HIV-1 (drug effects)</term>
<term>Humans</term>
<term>Magnetic Resonance Spectroscopy</term>
<term>Pyrimidinones (chemical synthesis)</term>
<term>Pyrimidinones (chemistry)</term>
<term>Pyrimidinones (pharmacology)</term>
<term>Reverse Transcriptase Inhibitors (chemical synthesis)</term>
<term>Reverse Transcriptase Inhibitors (chemistry)</term>
<term>Reverse Transcriptase Inhibitors (pharmacology)</term>
<term>Spectrometry, Mass, Electrospray Ionization</term>
<term>Spectroscopy, Fourier Transform Infrared</term>
<term>Structure-Activity Relationship</term>
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<keywords scheme="KwdFr" xml:lang="fr"><term>Cristallographie aux rayons X</term>
<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>Pyrimidinones ()</term>
<term>Pyrimidinones (pharmacologie)</term>
<term>Pyrimidinones (synthèse chimique)</term>
<term>Relation structure-activité</term>
<term>Spectrométrie de masse ESI</term>
<term>Spectroscopie infrarouge à transformée de Fourier</term>
<term>Spectroscopie par résonance magnétique</term>
<term>Transcriptase inverse du VIH (antagonistes et inhibiteurs)</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term>
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<term>Reverse Transcriptase Inhibitors</term>
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<keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Transcriptase inverse du VIH</term>
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<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term>
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<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Inhibiteurs de la transcriptase inverse</term>
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<term>Crystallography, X-Ray</term>
<term>Humans</term>
<term>Magnetic Resonance Spectroscopy</term>
<term>Spectrometry, Mass, Electrospray Ionization</term>
<term>Spectroscopy, Fourier Transform Infrared</term>
<term>Structure-Activity Relationship</term>
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<term>Lignée cellulaire</term>
<term>Pyrimidinones</term>
<term>Relation structure-activité</term>
<term>Spectrométrie de masse ESI</term>
<term>Spectroscopie infrarouge à transformée de Fourier</term>
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<front><div type="abstract" xml:lang="en">A series of new 5-alkyl-2-benzylsulfanylpyrimidin-4(3H)-ones (5a-y) bearing different substituted arylmethyl moieties at the C-6 position of the pyrimidine core have been synthesized and evaluated for their in vitro activities against HIV-1 and HIV-2 in MT-4 cell cultures. The majority of the title compounds showed moderate to good activities against HIV-1 with an IC(50) range from 6.67 microM to 0.12 microM. Among them, 6-(3,5-dimethylbenzyl) analogue 5q exhibited the most potent anti-HIV-1 activity (IC(50)=0.12 microM, SI>2642), which was about 40-fold more active than the reference compounds 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine (HEPT) and 2',3'-dideoxyinosine (DDI). The structure-activity relationships (SARs) of these new congeners were further discussed.</div>
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<Abstract><AbstractText>A series of new 5-alkyl-2-benzylsulfanylpyrimidin-4(3H)-ones (5a-y) bearing different substituted arylmethyl moieties at the C-6 position of the pyrimidine core have been synthesized and evaluated for their in vitro activities against HIV-1 and HIV-2 in MT-4 cell cultures. The majority of the title compounds showed moderate to good activities against HIV-1 with an IC(50) range from 6.67 microM to 0.12 microM. Among them, 6-(3,5-dimethylbenzyl) analogue 5q exhibited the most potent anti-HIV-1 activity (IC(50)=0.12 microM, SI>2642), which was about 40-fold more active than the reference compounds 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine (HEPT) and 2',3'-dideoxyinosine (DDI). The structure-activity relationships (SARs) of these new congeners were further discussed.</AbstractText>
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