Synthesis of 2-(2-adamantyl)piperidines and structure anti-influenza virus a activity relationship study using a combination of NMR spectroscopy and molecular modeling
Identifieur interne : 001984 ( Main/Exploration ); précédent : 001983; suivant : 001985Synthesis of 2-(2-adamantyl)piperidines and structure anti-influenza virus a activity relationship study using a combination of NMR spectroscopy and molecular modeling
Auteurs : Antonios Kolocouris [Grèce] ; Dimitrios Tataridis [Grèce] ; George Fytas [Grèce] ; Thomas Mavromoustakos [Grèce] ; George B. Foscolos [Grèce] ; Nicolas Kolocouris [Grèce] ; Erik De Clercq [Belgique]Source :
- Bioorganic & Medicinal Chemistry Letters [ 0960-894X ] ; 1999.
Descripteurs français
- KwdFr :
- MESH :
- pharmacologie : Antiviraux, Pipéridines.
- synthèse chimique : Antiviraux, Pipéridines.
- Pascal (Inist)
- Adamantane dérivé, Animaux, Antiviral, Antiviraux, Chiens, Composé saturé, Composé tricyclique, Hétérocycle azote, In vitro, Influenzavirus A, Influenzavirus B, Lignée cellulaire, Modèle moléculaire, Modèles moléculaires, Modélisation, Pipéridine(2-[2-adamantyl]), Pipéridine(2-[2-adamantyl]-1-alkyl), Pipéridines, Relation structure activité, Spectroscopie par résonance magnétique, Synthèse chimique, Virus de la grippe A.
English descriptors
- KwdEn :
- Animals, Antiviral, Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cell Line, Chemical synthesis, Dogs, In vitro, Influenza A virus (drug effects), Influenzavirus A, Influenzavirus B, Magnetic Resonance Spectroscopy, Modeling, Models, Molecular, Molecular model, Nitrogen heterocycle, Piperidines (chemical synthesis), Piperidines (chemistry), Piperidines (pharmacology), Saturated compound, Structure activity relation, Tricyclic compound.
- MESH :
- chemical , chemical synthesis : Antiviral Agents, Piperidines.
- chemical , chemistry : Antiviral Agents, Piperidines.
- chemical , pharmacology : Antiviral Agents, Piperidines.
- drug effects : Influenza A virus.
- Animals, Cell Line, Dogs, Magnetic Resonance Spectroscopy, Models, Molecular.
- Teeft :
- Adamantane, Adamantane nucleus, Amantadine, Aminoadamantane heterocycles, Axial, Axial orientation, Biological activity, Bioorg, Chem, Clercq, Computational, Computational chemistry, Conformational, Conformational properties, Conformer, Conformers, Derivative, Energy conformers, Force field, Fytas, Heterocycle, Influenza, Influenza virus, Kolocouris, Lett, Parent piperidine, Pharmaceutical chemistry, Piperidine, Piperidine heterocycle, Piperidine heterocycles, Piperidines, Rimantadine.
Abstract
Abstract: The 2-(2-adamantyl)piperidines 13 and 15a-c were synthesized and evaluated for anti-influenza virus A and B activity. The parent N-H compound 13 was 3–4 times more active than amantadine and rimantadine against H2N2 influenza A. N-alkylation of 13 resulted in derivatives 15a-c that were devoid of biological activity. This dramatic reduction in biological activity may be attributed to the different conformational properties between N-H and N-alkyl piperidines, as deduced from the combination of computational chemistry and NMR spectroscopy.
2-(2-Adamantyl)piperidine 13 proved active against H2N2 influenza virus A. N-Alkylation resulted in inactive compounds 15a-c. This dramatic loss of activity could be attributed to comformational changes as indicated by computational analysis and NMR spectroscopy.gr1
Url:
DOI: 10.1016/S0960-894X(99)00631-9
Affiliations:
- Belgique, Grèce
- Attique (région), Province du Brabant flamand, Région flamande
- Athènes, Louvain
- Katholieke Universiteit Leuven
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Le document en format XML
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cellulaire</term><term>Modèles moléculaires</term><term>Pipéridines ()</term><term>Pipéridines (pharmacologie)</term><term>Pipéridines (synthèse chimique)</term><term>Spectroscopie par résonance magnétique</term><term>Virus de la grippe A ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Piperidines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Piperidines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Piperidines</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Influenza A virus</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term><term>Pipéridines</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" 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xml:lang="en">Abstract: The 2-(2-adamantyl)piperidines 13 and 15a-c were synthesized and evaluated for anti-influenza virus A and B activity. The parent N-H compound 13 was 3–4 times more active than amantadine and rimantadine against H2N2 influenza A. N-alkylation of 13 resulted in derivatives 15a-c that were devoid of biological activity. This dramatic reduction in biological activity may be attributed to the different conformational properties between N-H and N-alkyl piperidines, as deduced from the combination of computational chemistry and NMR spectroscopy.</div><div type="abstract">2-(2-Adamantyl)piperidine 13 proved active against H2N2 influenza virus A. N-Alkylation resulted in inactive compounds 15a-c. This dramatic loss of activity could be attributed to comformational changes as indicated by computational analysis and NMR spectroscopy.gr1 </div></front></TEI><affiliations><list><country><li>Belgique</li><li>Grèce</li></country><region><li>Attique (région)</li><li>Province du Brabant flamand</li><li>Région flamande</li></region><settlement><li>Athènes</li><li>Louvain</li></settlement><orgName><li>Katholieke Universiteit Leuven</li></orgName></list><tree><country name="Grèce"><region name="Attique (région)"><name sortKey="Kolocouris, Antonios" sort="Kolocouris, Antonios" uniqKey="Kolocouris A" first="Antonios" last="Kolocouris">Antonios Kolocouris</name></region><name sortKey="Foscolos, George B" sort="Foscolos, George B" uniqKey="Foscolos G" first="George B." last="Foscolos">George B. Foscolos</name><name sortKey="Fytas, George" sort="Fytas, George" uniqKey="Fytas G" first="George" last="Fytas">George Fytas</name><name sortKey="Fytas, George" sort="Fytas, George" uniqKey="Fytas G" first="George" last="Fytas">George Fytas</name><name sortKey="Kolocouris, Nicolas" sort="Kolocouris, Nicolas" uniqKey="Kolocouris N" first="Nicolas" last="Kolocouris">Nicolas Kolocouris</name><name sortKey="Mavromoustakos, Thomas" sort="Mavromoustakos, Thomas" uniqKey="Mavromoustakos T" first="Thomas" last="Mavromoustakos">Thomas Mavromoustakos</name><name sortKey="Tataridis, Dimitrios" sort="Tataridis, Dimitrios" uniqKey="Tataridis D" first="Dimitrios" last="Tataridis">Dimitrios Tataridis</name></country><country name="Belgique"><region name="Région flamande"><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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