Spiro[pyrrolidine-2,2'-adamantanes]: Synthesis, anti-influenza virus activity and conformational properties
Identifieur interne : 000057 ( PascalFrancis/Checkpoint ); précédent : 000056; suivant : 000058Spiro[pyrrolidine-2,2'-adamantanes]: Synthesis, anti-influenza virus activity and conformational properties
Auteurs : Ioannis Stylianakis [Grèce] ; Antonios Kolocouris [Grèce] ; Nicolas Kolocouris [Grèce] ; George Fytas [Grèce] ; George B. Foscolos [Grèce] ; Elizaveta Padalko [Belgique] ; Johan Neyts [Belgique] ; Erik De Clercq [Belgique]Source :
- Bioorganic & medicinal chemistry letters [ 0960-894X ] ; 2003.
Descripteurs français
- Pascal (Inist)
- Relation structure activité, Synthèse chimique, Hétérocycle azote, Composé tricyclique, Spirane, Isomère position, Amine secondaire, Amine tertiaire, Analyse conformationnelle, Antiviral, Influenzavirus A, In vitro, Spiro[adamantane-2:2p-pyrrolidine](méthyl), Spiro[adamantane-2:2p-pyrrolidine](diméthyl).
English descriptors
- KwdEn :
Abstract
Synthetic spiro[pyrrolidine-2,2'-adamantanes] 2, 3, 11, 15, 12, 16, 18, 20 were evaluated in vitro and found to be active anti-influenza virus A compounds; the effect of the position of C-Me pyrrolidine ring substituent on antiviral activity was examined. Pyrrolidine 5-Me substitution appears to be optimal for H2N2 strain activity. From the four different possible protonated conformers, experimental observation using NMR spectroscopy and molecular mechanics calculations demonstrated only a pair of conformers A+H (N-Me (ps-ax), C-Me (ps-eq)) and B+H ((N-Me ps-ax, C-Me ps-ax)) which can contribute to the biological activity of C-Me, N-Me protonated derivatives 15+H, 16+H and 20+H. The relative populations were calculated from NMR spectra. For compounds 15+H and 20+H conformer A+H (cis dimethyl orientation) is the major one whereas a similar population of conformers A+H and B+H (trans dimethyl orientation) was observed for compound 16+H. Since this new series is characterized by a lipophilic part, that is the pyrrolidine ring, in addition to adamantane, that can interact with influenza A M2 protein, an ultimate future goal would be the in vitro mapping of M2 lipophilic pocket.
Affiliations:
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Pascal:03-0303149Le document en format XML
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<series><title level="j" type="main">Bioorganic & medicinal chemistry letters</title>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term>
<term>Chemical synthesis</term>
<term>Conformational analysis</term>
<term>In vitro</term>
<term>Influenzavirus A</term>
<term>Nitrogen heterocycle</term>
<term>Position isomer</term>
<term>Secondary amine</term>
<term>Spiran</term>
<term>Structure activity relation</term>
<term>Tertiary amine</term>
<term>Tricyclic compound</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Relation structure activité</term>
<term>Synthèse chimique</term>
<term>Hétérocycle azote</term>
<term>Composé tricyclique</term>
<term>Spirane</term>
<term>Isomère position</term>
<term>Amine secondaire</term>
<term>Amine tertiaire</term>
<term>Analyse conformationnelle</term>
<term>Antiviral</term>
<term>Influenzavirus A</term>
<term>In vitro</term>
<term>Spiro[adamantane-2:2p-pyrrolidine](méthyl)</term>
<term>Spiro[adamantane-2:2p-pyrrolidine](diméthyl)</term>
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<front><div type="abstract" xml:lang="en">Synthetic spiro[pyrrolidine-2,2'-adamantanes] 2, 3, 11, 15, 12, 16, 18, 20 were evaluated in vitro and found to be active anti-influenza virus A compounds; the effect of the position of C-Me pyrrolidine ring substituent on antiviral activity was examined. Pyrrolidine 5-Me substitution appears to be optimal for H<sub>2</sub>
N<sub>2</sub>
strain activity. From the four different possible protonated conformers, experimental observation using NMR spectroscopy and molecular mechanics calculations demonstrated only a pair of conformers A<sup>+</sup>
H (N-Me (ps-ax), C-Me (ps-eq)) and B<sup>+</sup>
H ((N-Me ps-ax, C-Me ps-ax)) which can contribute to the biological activity of C-Me, N-Me protonated derivatives 15<sup>+</sup>
H, 16<sup>+</sup>
H and 20<sup>+</sup>
H. The relative populations were calculated from NMR spectra. For compounds 15<sup>+</sup>
H and 20<sup>+</sup>
H conformer A<sup>+</sup>
H (cis dimethyl orientation) is the major one whereas a similar population of conformers A<sup>+</sup>
H and B<sup>+</sup>
H (trans dimethyl orientation) was observed for compound 16<sup>+</sup>
H. Since this new series is characterized by a lipophilic part, that is the pyrrolidine ring, in addition to adamantane, that can interact with influenza A M<sup>2</sup>
protein, an ultimate future goal would be the in vitro mapping of M2 lipophilic pocket.</div>
</front>
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<fC01 i1="01" l="ENG"><s0>Synthetic spiro[pyrrolidine-2,2'-adamantanes] 2, 3, 11, 15, 12, 16, 18, 20 were evaluated in vitro and found to be active anti-influenza virus A compounds; the effect of the position of C-Me pyrrolidine ring substituent on antiviral activity was examined. Pyrrolidine 5-Me substitution appears to be optimal for H<sub>2</sub>
N<sub>2</sub>
strain activity. From the four different possible protonated conformers, experimental observation using NMR spectroscopy and molecular mechanics calculations demonstrated only a pair of conformers A<sup>+</sup>
H (N-Me (ps-ax), C-Me (ps-eq)) and B<sup>+</sup>
H ((N-Me ps-ax, C-Me ps-ax)) which can contribute to the biological activity of C-Me, N-Me protonated derivatives 15<sup>+</sup>
H, 16<sup>+</sup>
H and 20<sup>+</sup>
H. The relative populations were calculated from NMR spectra. For compounds 15<sup>+</sup>
H and 20<sup>+</sup>
H conformer A<sup>+</sup>
H (cis dimethyl orientation) is the major one whereas a similar population of conformers A<sup>+</sup>
H and B<sup>+</sup>
H (trans dimethyl orientation) was observed for compound 16<sup>+</sup>
H. Since this new series is characterized by a lipophilic part, that is the pyrrolidine ring, in addition to adamantane, that can interact with influenza A M<sup>2</sup>
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<s5>04</s5>
</fC03>
<fC03 i1="03" i2="X" l="ENG"><s0>Nitrogen heterocycle</s0>
<s5>04</s5>
</fC03>
<fC03 i1="03" i2="X" l="SPA"><s0>Heterociclo nitrógeno</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="FRE"><s0>Composé tricyclique</s0>
<s5>05</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG"><s0>Tricyclic compound</s0>
<s5>05</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA"><s0>Compuesto tricíclico</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="FRE"><s0>Spirane</s0>
<s5>06</s5>
</fC03>
<fC03 i1="05" i2="X" l="ENG"><s0>Spiran</s0>
<s5>06</s5>
</fC03>
<fC03 i1="05" i2="X" l="SPA"><s0>Espirano</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="FRE"><s0>Isomère position</s0>
<s5>07</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG"><s0>Position isomer</s0>
<s5>07</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA"><s0>Isómero posición</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE"><s0>Amine secondaire</s0>
<s5>08</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG"><s0>Secondary amine</s0>
<s5>08</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA"><s0>Amina secundaria</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Amine tertiaire</s0>
<s5>09</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG"><s0>Tertiary amine</s0>
<s5>09</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Amina terciaria</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Analyse conformationnelle</s0>
<s5>10</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>Conformational analysis</s0>
<s5>10</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Análisis conformacional</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>Antiviral</s0>
<s5>12</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>Antiviral</s0>
<s5>12</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>Antiviral</s0>
<s5>12</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE"><s0>Influenzavirus A</s0>
<s2>NW</s2>
<s5>13</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG"><s0>Influenzavirus A</s0>
<s2>NW</s2>
<s5>13</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA"><s0>Influenzavirus A</s0>
<s2>NW</s2>
<s5>13</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>In vitro</s0>
<s5>15</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG"><s0>In vitro</s0>
<s5>15</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA"><s0>In vitro</s0>
<s5>15</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Spiro[adamantane-2:2p-pyrrolidine](méthyl)</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>62</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>Spiro[adamantane-2:2p-pyrrolidine](diméthyl)</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>63</s5>
</fC03>
<fC07 i1="01" i2="X" l="FRE"><s0>Orthomyxoviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="01" i2="X" l="ENG"><s0>Orthomyxoviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="01" i2="X" l="SPA"><s0>Orthomyxoviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="FRE"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="ENG"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="SPA"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fN21><s1>202</s1>
</fN21>
<fN82><s1>PSI</s1>
</fN82>
</pA>
</standard>
</inist>
<affiliations><list><country><li>Belgique</li>
<li>Grèce</li>
</country>
<region><li>Province du Brabant flamand</li>
</region>
<settlement><li>Louvain</li>
</settlement>
<orgName><li>Katholieke Universiteit Leuven</li>
</orgName>
</list>
<tree><country name="Grèce"><noRegion><name sortKey="Stylianakis, Ioannis" sort="Stylianakis, Ioannis" uniqKey="Stylianakis I" first="Ioannis" last="Stylianakis">Ioannis Stylianakis</name>
</noRegion>
<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="Kolocouris, Antonios" sort="Kolocouris, Antonios" uniqKey="Kolocouris A" first="Antonios" last="Kolocouris">Antonios Kolocouris</name>
<name sortKey="Kolocouris, Nicolas" sort="Kolocouris, Nicolas" uniqKey="Kolocouris N" first="Nicolas" last="Kolocouris">Nicolas Kolocouris</name>
</country>
<country name="Belgique"><region name="Province du Brabant flamand"><name sortKey="Padalko, Elizaveta" sort="Padalko, Elizaveta" uniqKey="Padalko E" first="Elizaveta" last="Padalko">Elizaveta Padalko</name>
</region>
<name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name>
<name sortKey="Neyts, Johan" sort="Neyts, Johan" uniqKey="Neyts J" first="Johan" last="Neyts">Johan Neyts</name>
</country>
</tree>
</affiliations>
</record>
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