SrasV1, Main, Exploration, bibRecord, 003460

Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 1. Parallel synthesis, molecular modelling and structure-activity relationship studies on 0-[2-(hetero)arylethyl]-N-phenylthiocarbamates

Identifieur interne : 003460 ( Main/Exploration ); précédent : 003459; suivant : 003461

Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 1. Parallel synthesis, molecular modelling and structure-activity relationship studies on 0-[2-(hetero)arylethyl]-N-phenylthiocarbamates

Auteurs : Sara Cesarini [Italie] ; Andrea Spallarossa [Italie] ; Angelo Ranise [Italie] ; Paola Fossa [Italie] ; Paolo La Colla [Italie] ; Giuseppina Sanna [Italie] ; Gabriella Collu [Italie] ; Roberta Loddo [Italie]

Source :

Bioorganic & medicinal chemistry [ 0968-0896 ] ; 2008.

RBID : Pascal:08-0345082

Descripteurs français

Pascal (Inist)
- Antiviral, Chimie combinatoire, Composé benzénique, Composé non nucléoside, Cytotoxicité, In vitro, Inhibiteur enzyme, Inhibiteur reverse transcriptase, Modèle moléculaire, Modélisation, RNA-directed DNA polymerase, Relation structure activité, Résistance, Synthèse chimique, Thiocarbamate organique, Thiocarbamate(N-[4-chlorophényl]-O-[2-méthoxyphénéthyl]), Thiocarbamate(O-[3-méthoxyphénéthyl]-N-[4-nitrophényl]), Virus HIV1, Inhibiteur reverse transcriptase, Chimie combinatoire, Synthèse chimique, Modèle moléculaire, Modélisation, Relation structure activité, Thiocarbamate organique, In vitro, Dérivé de la pyridine, Dérivé du thiophène, Inhibiteur enzyme, Antiviral, RNA-directed DNA polymerase, Thiocarbamate(N-[3-nitrophényl]-O-[2-pyridyléthyl]), Thiocarbamate(N-[4-bromophényl]-O-[2-pyridyléthyl]).

English descriptors

KwdEn :
- Antiviral, Benzenic compound, Chemical synthesis, Combinatorial chemistry, Cytotoxicity, Enzyme inhibitor, HIV-1 virus, In vitro, Modeling, Molecular model, Non nucleoside compound, Organic thiocarbamate, Pyridine derivatives, RNA-directed DNA polymerase, Resistance, Reverse transcriptase inhibitor, Structure activity relation, Thiophene derivatives.

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 EC₅₀ 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.

Affiliations:

Italie

Le document en format XML

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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term>
<term>Benzenic compound</term>
<term>Chemical synthesis</term>
<term>Combinatorial chemistry</term>
<term>Cytotoxicity</term>
<term>Enzyme inhibitor</term>
<term>HIV-1 virus</term>
<term>In vitro</term>
<term>Modeling</term>
<term>Molecular model</term>
<term>Non nucleoside compound</term>
<term>Organic thiocarbamate</term>
<term>Pyridine derivatives</term>
<term>RNA-directed DNA polymerase</term>
<term>Resistance</term>
<term>Reverse transcriptase inhibitor</term>
<term>Structure activity relation</term>
<term>Thiophene derivatives</term>
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<keywords scheme="Pascal" xml:lang="fr"><term>Antiviral</term>
<term>Chimie combinatoire</term>
<term>Composé benzénique</term>
<term>Composé non nucléoside</term>
<term>Cytotoxicité</term>
<term>In vitro</term>
<term>Inhibiteur enzyme</term>
<term>Inhibiteur reverse transcriptase</term>
<term>Modèle moléculaire</term>
<term>Modélisation</term>
<term>RNA-directed DNA polymerase</term>
<term>Relation structure activité</term>
<term>Résistance</term>
<term>Synthèse chimique</term>
<term>Thiocarbamate organique</term>
<term>Thiocarbamate(N-[4-chlorophényl]-O-[2-méthoxyphénéthyl])</term>
<term>Thiocarbamate(O-[3-méthoxyphénéthyl]-N-[4-nitrophényl])</term>
<term>Virus HIV1</term>
<term>Inhibiteur reverse transcriptase</term>
<term>Chimie combinatoire</term>
<term>Synthèse chimique</term>
<term>Modèle moléculaire</term>
<term>Modélisation</term>
<term>Relation structure activité</term>
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<term>Dérivé de la pyridine</term>
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<term>Antiviral</term>
<term>RNA-directed DNA polymerase</term>
<term>Thiocarbamate(N-[3-nitrophényl]-O-[2-pyridyléthyl])</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<sub>50</sub>
 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>
</TEI>
<affiliations><list><country><li>Italie</li>
</country>
</list>
<tree><country name="Italie"><noRegion><name sortKey="Cesarini, Sara" sort="Cesarini, Sara" uniqKey="Cesarini S" first="Sara" last="Cesarini">Sara Cesarini</name>
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<name sortKey="Collu, Gabriella" sort="Collu, Gabriella" uniqKey="Collu G" first="Gabriella" last="Collu">Gabriella Collu</name>
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<name sortKey="Ranise, Angelo" sort="Ranise, Angelo" uniqKey="Ranise A" first="Angelo" last="Ranise">Angelo Ranise</name>
<name sortKey="Sanna, Giuseppina" sort="Sanna, Giuseppina" uniqKey="Sanna G" first="Giuseppina" last="Sanna">Giuseppina Sanna</name>
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Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 1. Parallel synthesis, molecular modelling and structure-activity relationship studies on 0-[2-(hetero)arylethyl]-N-phenylthiocarbamates

Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 1. Parallel synthesis, molecular modelling and structure-activity relationship studies on 0-[2-(hetero)arylethyl]-N-phenylthiocarbamates

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