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Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Parallel synthesis, molecular modelling and structure-activity relationship studies on analogues of O-(2-phenylethyl)-N-phenylthiocarbamate.

Identifieur interne : 001C28 ( PubMed/Curation ); précédent : 001C27; suivant : 001C29

Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Parallel synthesis, molecular modelling and structure-activity relationship studies on analogues of O-(2-phenylethyl)-N-phenylthiocarbamate.

Auteurs : Sara Cesarini [Italie] ; Andrea Spallarossa ; Angelo Ranise ; Olga Bruno ; Paolo La Colla ; Barbara Secci ; Gabriella Collu ; Roberta Loddo

Source :

Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2008.

RBID : pubmed:18226533

Descripteurs français

English descriptors

KwdEn :
- HIV-1 (drug effects), HIV-1 (enzymology), Models, Molecular, Molecular Structure, Nucleosides (chemistry), 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.
- chemical , pharmacology : Reverse Transcriptase Inhibitors, Thiocarbamates.
- Models, Molecular, Molecular Structure, Structure-Activity Relationship.

Abstract

To acquire further insight into the structure-activity relationship (SAR) of the thiocarbamates (TCs) described in the preceding work, 57 analogues of the lead compound O-(2-phenylethyl)-N-phenylthiocarbamate I were prepared by parallel solution-phase synthesis. We varied the 2-phenylethyl moiety (mono-substitution on the phenyl ring and modification of the ethyl linker), keeping constant the N-phenyl ring substitutions which have given the best results in the previous series. Most of the new TCs inhibited wild-type HIV-1 at micro- and nanomolar concentrations in MT-4 cell-based assays. Some TCs were also active at micromolar concentrations against the Y181C and/or K103N/Y181C resistant mutants. The SARs were rationalized by docking simulations.

DOI: 10.1016/j.bmc.2007.12.046
PubMed: 18226533

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<author><name sortKey="Cesarini, Sara" sort="Cesarini, Sara" uniqKey="Cesarini S" first="Sara" last="Cesarini">Sara Cesarini</name>
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<author><name sortKey="Secci, Barbara" sort="Secci, Barbara" uniqKey="Secci B" first="Barbara" last="Secci">Barbara Secci</name>
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<term>Molecular Structure</term>
<term>Nucleosides (chemistry)</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>
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<term>Thiocarbamates (chemistry)</term>
<term>Thiocarbamates (pharmacology)</term>
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<term>Inhibiteurs de la transcriptase inverse (pharmacologie)</term>
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<term>Modèles moléculaires</term>
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<term>Structure moléculaire</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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<front><div type="abstract" xml:lang="en">To acquire further insight into the structure-activity relationship (SAR) of the thiocarbamates (TCs) described in the preceding work, 57 analogues of the lead compound O-(2-phenylethyl)-N-phenylthiocarbamate I were prepared by parallel solution-phase synthesis. We varied the 2-phenylethyl moiety (mono-substitution on the phenyl ring and modification of the ethyl linker), keeping constant the N-phenyl ring substitutions which have given the best results in the previous series. Most of the new TCs inhibited wild-type HIV-1 at micro- and nanomolar concentrations in MT-4 cell-based assays. Some TCs were also active at micromolar concentrations against the Y181C and/or K103N/Y181C resistant mutants. The SARs were rationalized by docking simulations.</div>
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Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Parallel synthesis, molecular modelling and structure-activity relationship studies on analogues of O-(2-phenylethyl)-N-phenylthiocarbamate.

Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Parallel synthesis, molecular modelling and structure-activity relationship studies on analogues of O-(2-phenylethyl)-N-phenylthiocarbamate.

Source :

Descripteurs français

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Abstract

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