Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 1: Parallel synthesis, molecular modelling and structure-activity relationship studies on O-[2-(hetero)arylethyl]-N-phenylthiocarbamates.
Identifieur interne : 001B63 ( Ncbi/Merge ); précédent : 001B62; suivant : 001B64Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 1: Parallel synthesis, molecular modelling and structure-activity relationship studies on O-[2-(hetero)arylethyl]-N-phenylthiocarbamates.
Auteurs : Sara Cesarini [Italie] ; Andrea Spallarossa ; Angelo Ranise ; Paola Fossa ; Paolo La Colla ; Giuseppina Sanna ; Gabriella Collu ; Roberta LoddoSource :
- Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2008.
Descripteurs français
- KwdFr :
- Inhibiteurs de la transcriptase inverse (), Inhibiteurs de la transcriptase inverse (pharmacologie), Inhibiteurs de la transcriptase inverse (synthèse chimique), Modèles moléculaires, Mutation (génétique), Nucléosides (), RNA-directed DNA polymerase (génétique), RNA-directed DNA polymerase (métabolisme), Relation structure-activité, Structure moléculaire, Thiocarbamates (), Thiocarbamates (pharmacologie), Thiocarbamates (synthèse chimique), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (enzymologie), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (génétique).
- MESH :
- enzymologie : VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
- génétique : Mutation, RNA-directed DNA polymerase, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
- métabolisme : RNA-directed DNA polymerase.
- pharmacologie : Inhibiteurs de la transcriptase inverse, Thiocarbamates.
- synthèse chimique : Inhibiteurs de la transcriptase inverse, Thiocarbamates.
- Inhibiteurs de la transcriptase inverse, Modèles moléculaires, Nucléosides, Relation structure-activité, Structure moléculaire, Thiocarbamates, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
English descriptors
- KwdEn :
- HIV-1 (drug effects), HIV-1 (enzymology), HIV-1 (genetics), Models, Molecular, Molecular Structure, Mutation (genetics), Nucleosides (chemistry), RNA-Directed DNA Polymerase (genetics), RNA-Directed DNA Polymerase (metabolism), Reverse Transcriptase Inhibitors (chemical synthesis), Reverse Transcriptase Inhibitors (chemistry), Reverse Transcriptase Inhibitors (pharmacology), Structure-Activity Relationship, Thiocarbamates (chemical synthesis), Thiocarbamates (chemistry), Thiocarbamates (pharmacology).
- MESH :
- chemical , chemical synthesis : Reverse Transcriptase Inhibitors, Thiocarbamates.
- chemical , chemistry : Nucleosides, Reverse Transcriptase Inhibitors, Thiocarbamates.
- drug effects : HIV-1.
- enzymology : HIV-1.
- genetics : HIV-1, Mutation, RNA-Directed DNA Polymerase.
- chemical , metabolism : RNA-Directed DNA Polymerase.
- chemical , pharmacology : Reverse Transcriptase Inhibitors, Thiocarbamates.
- Models, Molecular, Molecular Structure, Structure-Activity Relationship.
Abstract
In order to expand the structure-activity relationship (SAR) studies on Thiocarbamates (TCs), a recently discovered class of potent non-nucleoside HIV-1 reverse transcriptase inhibitors, 38 analogues of the lead O-[2-(2-pyridyl)ethyl]-N-phenylthiocarbamate 1 were prepared by parallel solution-phase synthesis. The SAR strategy was focused on the variation (mono- and disubstitution) of the N-phenyl ring and the replacement of the 2-pyridyl with 4-pyridyl, 2-thienyl and phenyl rings. The majority of the new TCs proved to prevent the wild-type HIV-1 multiplication in MT-4 cell culture and the most potent congeners displayed an EC(50) value of 100 nM. Two TCs were active also at micromolar concentrations against the Y181C- and/or K103N/Y181C-resistant mutants. Docking simulations helped to rationalize the SARs.
DOI: 10.1016/j.bmc.2007.12.050
PubMed: 18226532
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pubmed:18226532Le document en format XML
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<term>HIV-1 (enzymology)</term>
<term>HIV-1 (genetics)</term>
<term>Models, Molecular</term>
<term>Molecular Structure</term>
<term>Mutation (genetics)</term>
<term>Nucleosides (chemistry)</term>
<term>RNA-Directed DNA Polymerase (genetics)</term>
<term>RNA-Directed DNA Polymerase (metabolism)</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>Thiocarbamates (chemical synthesis)</term>
<term>Thiocarbamates (chemistry)</term>
<term>Thiocarbamates (pharmacology)</term>
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<keywords scheme="KwdFr" xml:lang="fr"><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>Modèles moléculaires</term>
<term>Mutation (génétique)</term>
<term>Nucléosides ()</term>
<term>RNA-directed DNA polymerase (génétique)</term>
<term>RNA-directed DNA polymerase (métabolisme)</term>
<term>Relation structure-activité</term>
<term>Structure moléculaire</term>
<term>Thiocarbamates ()</term>
<term>Thiocarbamates (pharmacologie)</term>
<term>Thiocarbamates (synthèse chimique)</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (enzymologie)</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (génétique)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Reverse Transcriptase Inhibitors</term>
<term>Thiocarbamates</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Nucleosides</term>
<term>Reverse Transcriptase Inhibitors</term>
<term>Thiocarbamates</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="enzymologie" xml:lang="fr"><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term>
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<term>RNA-Directed DNA Polymerase</term>
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<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term>
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<term>Thiocarbamates</term>
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<term>Relation structure-activité</term>
<term>Structure moléculaire</term>
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<front><div type="abstract" xml:lang="en">In order to expand the structure-activity relationship (SAR) studies on Thiocarbamates (TCs), a recently discovered class of potent non-nucleoside HIV-1 reverse transcriptase inhibitors, 38 analogues of the lead O-[2-(2-pyridyl)ethyl]-N-phenylthiocarbamate 1 were prepared by parallel solution-phase synthesis. The SAR strategy was focused on the variation (mono- and disubstitution) of the N-phenyl ring and the replacement of the 2-pyridyl with 4-pyridyl, 2-thienyl and phenyl rings. The majority of the new TCs proved to prevent the wild-type HIV-1 multiplication in MT-4 cell culture and the most potent congeners displayed an EC(50) value of 100 nM. Two TCs were active also at micromolar concentrations against the Y181C- and/or K103N/Y181C-resistant mutants. Docking simulations helped to rationalize the SARs.</div>
</front>
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<Abstract><AbstractText>In order to expand the structure-activity relationship (SAR) studies on Thiocarbamates (TCs), a recently discovered class of potent non-nucleoside HIV-1 reverse transcriptase inhibitors, 38 analogues of the lead O-[2-(2-pyridyl)ethyl]-N-phenylthiocarbamate 1 were prepared by parallel solution-phase synthesis. The SAR strategy was focused on the variation (mono- and disubstitution) of the N-phenyl ring and the replacement of the 2-pyridyl with 4-pyridyl, 2-thienyl and phenyl rings. The majority of the new TCs proved to prevent the wild-type HIV-1 multiplication in MT-4 cell culture and the most potent congeners displayed an EC(50) value of 100 nM. Two TCs were active also at micromolar concentrations against the Y181C- and/or K103N/Y181C-resistant mutants. Docking simulations helped to rationalize the SARs.</AbstractText>
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<ForeName>Sara</ForeName>
<Initials>S</Initials>
<AffiliationInfo><Affiliation>Dipartimento di Scienze Farmaceutiche, Università di Genova, Viale Benedetto XV 3, I-16132 Genova, Italy. sara.cesarini@unige.it</Affiliation>
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