SrasV1, Main, Merge, bibRecord, 002F75

Parallel synthesis, molecular modelling and further structure-activity relationship studies of new acylthiocarbamates as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

Identifieur interne : 002F75 ( Main/Merge ); précédent : 002F74; suivant : 002F76

Parallel synthesis, molecular modelling and further structure-activity relationship studies of new acylthiocarbamates as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

Auteurs : Andrea Spallarossa [Italie] ; Sara Cesarini [Italie] ; Angelo Ranise [Italie] ; Silvia Schenone [Italie] ; Olga Bruno [Italie] ; Alberto Borassi [Italie] ; Paolo La Colla [Italie] ; Margherita Pezzullo [Italie] ; Giuseppina Sanna [Italie] ; Gabriella Collu [Italie] ; Barbara Secci [Italie] ; Roberta Loddo [Italie]

Source :

European journal of medicinal chemistry [ 0223-5234 ] ; 2009.

RBID : Pascal:09-0279028

Descripteurs français

Pascal (Inist)
- Chimie combinatoire, Synthèse chimique, Modèle moléculaire, Modélisation, Relation structure activité, Thiocarbamate organique, Composé non nucléoside, Virus HIV1, Inhibiteur reverse transcriptase, Dérivé du benzène, Halogène Composé organique, Composé nitro, In vitro, Complexe enzyme inhibiteur, Antiviral, Inhibiteur enzyme, RNA-directed DNA polymerase, Imide, Phtalimide dérivé, Thiocarbamate(N-[2-chlorophényl]-N-[3-nitrobenzoyl]-O-[2-phtalidimidoéthyl]).

English descriptors

KwdEn :
- Antiviral, Benzene derivatives, Chemical synthesis, Combinatorial chemistry, Enzyme inhibitor, HIV-1 virus, Halogen Organic compounds, Imide, In vitro, Inhibitor enzyme complex, Modeling, Molecular model, Nitro compound, Non nucleoside compound, Organic thiocarbamate, RNA-directed DNA polymerase, Reverse transcriptase inhibitor, Structure activity relation.

Abstract

The structure-activity relationships (SARs) of acylthiocarbamates (ATCs), a new class of non-nucleoside HIV-1 reverse transcriptase inhibitors, have been expanded. Sixty-six new analogues were prepared by parallel solution-phase synthesis. In general, the potency of new ATCs was better than that of the first series and O-[2-phthalimidoethyl] 4-chlorophenyl(3-nitrobenzoyl) thiocarbamate turned out to be the most potent ATC so far synthesized (ECso = 1.5 nM). Several ATCs were active at micromolar concentrations against HIV-1 strains carrying the RT Y181C mutation and one of them was also moderately active against the K103R variant. Docking simulations were carried out to rationalize the most relevant SARs.

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Pascal:09-0279028

Le document en format XML

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<series><title level="j" type="main">European journal of medicinal chemistry</title>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term>
<term>Benzene derivatives</term>
<term>Chemical synthesis</term>
<term>Combinatorial chemistry</term>
<term>Enzyme inhibitor</term>
<term>HIV-1 virus</term>
<term>Halogen Organic compounds</term>
<term>Imide</term>
<term>In vitro</term>
<term>Inhibitor enzyme complex</term>
<term>Modeling</term>
<term>Molecular model</term>
<term>Nitro compound</term>
<term>Non nucleoside compound</term>
<term>Organic thiocarbamate</term>
<term>RNA-directed DNA polymerase</term>
<term>Reverse transcriptase inhibitor</term>
<term>Structure activity relation</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Chimie combinatoire</term>
<term>Synthèse chimique</term>
<term>Modèle moléculaire</term>
<term>Modélisation</term>
<term>Relation structure activité</term>
<term>Thiocarbamate organique</term>
<term>Composé non nucléoside</term>
<term>Virus HIV1</term>
<term>Inhibiteur reverse transcriptase</term>
<term>Dérivé du benzène</term>
<term>Halogène Composé organique</term>
<term>Composé nitro</term>
<term>In vitro</term>
<term>Complexe enzyme inhibiteur</term>
<term>Antiviral</term>
<term>Inhibiteur enzyme</term>
<term>RNA-directed DNA polymerase</term>
<term>Imide</term>
<term>Phtalimide dérivé</term>
<term>Thiocarbamate(N-[2-chlorophényl]-N-[3-nitrobenzoyl]-O-[2-phtalidimidoéthyl])</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">The structure-activity relationships (SARs) of acylthiocarbamates (ATCs), a new class of non-nucleoside HIV-1 reverse transcriptase inhibitors, have been expanded. Sixty-six new analogues were prepared by parallel solution-phase synthesis. In general, the potency of new ATCs was better than that of the first series and O-[2-phthalimidoethyl] 4-chlorophenyl(3-nitrobenzoyl) thiocarbamate turned out to be the most potent ATC so far synthesized (ECso = 1.5 nM). Several ATCs were active at micromolar concentrations against HIV-1 strains carrying the RT Y181C mutation and one of them was also moderately active against the K103R variant. Docking simulations were carried out to rationalize the most relevant SARs.</div>
</front>
</TEI>
<affiliations><list><country><li>Italie</li>
</country>
</list>
<tree><country name="Italie"><noRegion><name sortKey="Spallarossa, Andrea" sort="Spallarossa, Andrea" uniqKey="Spallarossa A" first="Andrea" last="Spallarossa">Andrea Spallarossa</name>
</noRegion>
<name sortKey="Borassi, Alberto" sort="Borassi, Alberto" uniqKey="Borassi A" first="Alberto" last="Borassi">Alberto Borassi</name>
<name sortKey="Bruno, Olga" sort="Bruno, Olga" uniqKey="Bruno O" first="Olga" last="Bruno">Olga Bruno</name>
<name sortKey="Cesarini, Sara" sort="Cesarini, Sara" uniqKey="Cesarini S" first="Sara" last="Cesarini">Sara Cesarini</name>
<name sortKey="Collu, Gabriella" sort="Collu, Gabriella" uniqKey="Collu G" first="Gabriella" last="Collu">Gabriella Collu</name>
<name sortKey="La Colla, Paolo" sort="La Colla, Paolo" uniqKey="La Colla P" first="Paolo" last="La Colla">Paolo La Colla</name>
<name sortKey="Loddo, Roberta" sort="Loddo, Roberta" uniqKey="Loddo R" first="Roberta" last="Loddo">Roberta Loddo</name>
<name sortKey="Pezzullo, Margherita" sort="Pezzullo, Margherita" uniqKey="Pezzullo M" first="Margherita" last="Pezzullo">Margherita Pezzullo</name>
<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>
<name sortKey="Schenone, Silvia" sort="Schenone, Silvia" uniqKey="Schenone S" first="Silvia" last="Schenone">Silvia Schenone</name>
<name sortKey="Secci, Barbara" sort="Secci, Barbara" uniqKey="Secci B" first="Barbara" last="Secci">Barbara Secci</name>
</country>
</tree>
</affiliations>
</record>

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Parallel synthesis, molecular modelling and further structure-activity relationship studies of new acylthiocarbamates as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

Parallel synthesis, molecular modelling and further structure-activity relationship studies of new acylthiocarbamates as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

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