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 : 001A31 ( Main/Merge ); précédent : 001A30; suivant : 001A32Synthesis 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.
English descriptors
- 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
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<term>Axial orientation</term>
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<term>Influenza virus</term>
<term>Kolocouris</term>
<term>Lett</term>
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<front><div type="abstract" 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>
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