H2N2V1, PascalFrancis, Corpus, bibRecord, 000071

Novel 3-(2-adamantyl)pyrrolidines with potent activity against influenza A virus : Identification of aminoadamantane derivatives bearing two pharmacophoric amine groups

Identifieur interne : 000071 ( PascalFrancis/Corpus ); précédent : 000070; suivant : 000072

Novel 3-(2-adamantyl)pyrrolidines with potent activity against influenza A virus : Identification of aminoadamantane derivatives bearing two pharmacophoric amine groups

Auteurs : George Stamatiou ; Antonios Kolocouris ; Nicolas Kolocouris ; George Fytas ; George B. Foscolos ; Johan Neyts ; Erik De Clercq

Source :

Bioorganic & medicinal chemistry letters [ 0960-894X ] ; 2001.

RBID : Pascal:01-0423706

Descripteurs français

Pascal (Inist)
- Relation structure activité, Synthèse chimique, Composé tricyclique, Composé saturé, Hétérocycle azote, Diamine, Amine tertiaire, Antiviral, Virus grippal A, In vitro, Modélisation, Modèle moléculaire, Méthode dynamique moléculaire, Analyse conformationnelle, Adamamtane dérivé, Pyrrolidine(3-[2-adamantyl]-1-[2-(dialkylamino)éthyl]).

English descriptors

KwdEn :
- Antiviral, Chemical synthesis, Conformational analysis, Diamine, In vitro, Influenza A virus, Modeling, Molecular dynamics method, Molecular model, Nitrogen heterocycle, Saturated compound, Structure activity relation, Tertiary amine, Tricyclic compound.

Abstract

The 3(2-adamantyl)pyrrolidines 8a g, 14 were synthesized and evaluated for activity against influenza A virus. The parent N H compound 14 was several times more active than amantadine against H₂N₂ and H₃N₂ influenza A virus. The combined use of NMR spectroscopy and computational chemistry showed that the conformation around the pyrrolidine-adamantyl carbon carbon bond is trans and the pyrrolidine heterocycle has an envelope conformation with C-2 out of the plane of the other ring atoms. N-Dialkylaminoethyl substitution of compound 14 resulted in the potent diamine analogues 8e,f,g. Interestingly, their lactam amine precursors were also active. Compounds 8e,f,g are the first adamantane derivatives, bearing two amine groups, reported to be active against influenza A virus.

Notice en format standard (ISO 2709)

Pour connaître la documentation sur le format Inist Standard.

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A03		`1`		`@0 Bioorg. med. chem. lett.`
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A08	`01`	`1`	`ENG`	`@1 Novel 3-(2-adamantyl)pyrrolidines with potent activity against influenza A virus : Identification of aminoadamantane derivatives bearing two pharmacophoric amine groups`
A11	`01`	`1`		`@1 STAMATIOU (George)`
A11	`02`	`1`		`@1 KOLOCOURIS (Antonios)`
A11	`03`	`1`		`@1 KOLOCOURIS (Nicolas)`
A11	`04`	`1`		`@1 FYTAS (George)`
A11	`05`	`1`		`@1 FOSCOLOS (George B.)`
A11	`06`	`1`		`@1 NEYTS (Johan)`
A11	`07`	`1`		`@1 DE CLERCQ (Erik)`
A14	`01`			`@1 School of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Panepistimioupoli-Zografou @2 15771 Athens @3 GRC @Z 1 aut. @Z 2 aut. @Z 3 aut. @Z 4 aut. @Z 5 aut.`
A14	`02`			`@1 Rega Institute for Medical Research, Katholieke Universiteit Leuven @2 3000 Leuven @3 BEL @Z 6 aut. @Z 7 aut.`
A20				`@1 2137-2142`
A21				`@1 2001`
A23	`01`			`@0 ENG`
A43	`01`			`@1 INIST @2 22446 @5 354000095772720180`
A44				`@0 0000 @1 © 2001 INIST-CNRS. All rights reserved.`
A47	`01`	`1`		`@0 01-0423706`
A60				`@1 P`
A61				`@0 A`
A64	`01`	`1`		`@0 Bioorganic & medicinal chemistry letters`
A66	`01`			`@0 GBR`
A99				`@0 1/2 p. ref. et notes`
C01	`01`		`ENG`	@0 The 3(2-adamantyl)pyrrolidines 8a g, 14 were synthesized and evaluated for activity against influenza A virus. The parent N H compound 14 was several times more active than amantadine against H₂N₂ and H₃N₂ influenza A virus. The combined use of NMR spectroscopy and computational chemistry showed that the conformation around the pyrrolidine-adamantyl carbon carbon bond is trans and the pyrrolidine heterocycle has an envelope conformation with C-2 out of the plane of the other ring atoms. N-Dialkylaminoethyl substitution of compound 14 resulted in the potent diamine analogues 8e,f,g. Interestingly, their lactam amine precursors were also active. Compounds 8e,f,g are the first adamantane derivatives, bearing two amine groups, reported to be active against influenza A virus.
C02	`01`	`X`		`@0 002B02S05`
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C03	`01`	`X`	`ENG`	`@0 Structure activity relation @5 01`
C03	`01`	`X`	`SPA`	`@0 Relación estructura actividad @5 01`
C03	`02`	`X`	`FRE`	`@0 Synthèse chimique @5 02`
C03	`02`	`X`	`ENG`	`@0 Chemical synthesis @5 02`
C03	`02`	`X`	`SPA`	`@0 Síntesis química @5 02`
C03	`03`	`X`	`FRE`	`@0 Composé tricyclique @5 03`
C03	`03`	`X`	`ENG`	`@0 Tricyclic compound @5 03`
C03	`03`	`X`	`SPA`	`@0 Compuesto tricíclico @5 03`
C03	`04`	`X`	`FRE`	`@0 Composé saturé @5 04`
C03	`04`	`X`	`ENG`	`@0 Saturated compound @5 04`
C03	`04`	`X`	`SPA`	`@0 Compuesto saturado @5 04`
C03	`05`	`X`	`FRE`	`@0 Hétérocycle azote @5 05`
C03	`05`	`X`	`ENG`	`@0 Nitrogen heterocycle @5 05`
C03	`05`	`X`	`SPA`	`@0 Heterociclo nitrógeno @5 05`
C03	`06`	`X`	`FRE`	`@0 Diamine @5 06`
C03	`06`	`X`	`ENG`	`@0 Diamine @5 06`
C03	`06`	`X`	`SPA`	`@0 Diamina @5 06`
C03	`07`	`X`	`FRE`	`@0 Amine tertiaire @5 07`
C03	`07`	`X`	`ENG`	`@0 Tertiary amine @5 07`
C03	`07`	`X`	`SPA`	`@0 Amina terciaria @5 07`
C03	`08`	`X`	`FRE`	`@0 Antiviral @5 09`
C03	`08`	`X`	`ENG`	`@0 Antiviral @5 09`
C03	`08`	`X`	`SPA`	`@0 Antiviral @5 09`
C03	`09`	`X`	`FRE`	`@0 Virus grippal A @2 NW @5 10`
C03	`09`	`X`	`ENG`	`@0 Influenza A virus @2 NW @5 10`
C03	`09`	`X`	`SPA`	`@0 Influenza A virus @2 NW @5 10`
C03	`10`	`X`	`FRE`	`@0 In vitro @5 12`
C03	`10`	`X`	`ENG`	`@0 In vitro @5 12`
C03	`10`	`X`	`SPA`	`@0 In vitro @5 12`
C03	`11`	`X`	`FRE`	`@0 Modélisation @5 17`
C03	`11`	`X`	`ENG`	`@0 Modeling @5 17`
C03	`11`	`X`	`SPA`	`@0 Modelización @5 17`
C03	`12`	`X`	`FRE`	`@0 Modèle moléculaire @5 18`
C03	`12`	`X`	`ENG`	`@0 Molecular model @5 18`
C03	`12`	`X`	`SPA`	`@0 Modelo molecular @5 18`
C03	`13`	`X`	`FRE`	`@0 Méthode dynamique moléculaire @5 19`
C03	`13`	`X`	`ENG`	`@0 Molecular dynamics method @5 19`
C03	`13`	`X`	`SPA`	`@0 Método dinámico molecular @5 19`
C03	`14`	`X`	`FRE`	`@0 Analyse conformationnelle @5 20`
C03	`14`	`X`	`ENG`	`@0 Conformational analysis @5 20`
C03	`14`	`X`	`SPA`	`@0 Análisis conformacional @5 20`
C03	`15`	`X`	`FRE`	`@0 Adamamtane dérivé @2 NK @4 INC @5 62`
C03	`16`	`X`	`FRE`	`@0 Pyrrolidine(3-[2-adamantyl]-1-[2-(dialkylamino)éthyl]) @2 NK @4 INC @5 63`
C07	`01`	`X`	`FRE`	`@0 Influenzavirus A @2 NW`
C07	`01`	`X`	`ENG`	`@0 Influenzavirus A @2 NW`
C07	`01`	`X`	`SPA`	`@0 Influenzavirus A @2 NW`
C07	`02`	`X`	`FRE`	`@0 Orthomyxoviridae @2 NW`
C07	`02`	`X`	`ENG`	`@0 Orthomyxoviridae @2 NW`
C07	`02`	`X`	`SPA`	`@0 Orthomyxoviridae @2 NW`
C07	`03`	`X`	`FRE`	`@0 Virus @2 NW`
C07	`03`	`X`	`ENG`	`@0 Virus @2 NW`
C07	`03`	`X`	`SPA`	`@0 Virus @2 NW`
N21				`@1 295`

Format Inist (serveur)

NO :	PASCAL 01-0423706 INIST
ET :	Novel 3-(2-adamantyl)pyrrolidines with potent activity against influenza A virus : Identification of aminoadamantane derivatives bearing two pharmacophoric amine groups
AU :	STAMATIOU (George); KOLOCOURIS (Antonios); KOLOCOURIS (Nicolas); FYTAS (George); FOSCOLOS (George B.); NEYTS (Johan); DE CLERCQ (Erik)
AF :	School of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Panepistimioupoli-Zografou/15771 Athens/Grèce (1 aut., 2 aut., 3 aut., 4 aut., 5 aut.); Rega Institute for Medical Research, Katholieke Universiteit Leuven/3000 Leuven/Belgique (6 aut., 7 aut.)
DT :	Publication en série; Niveau analytique
SO :	Bioorganic & medicinal chemistry letters; ISSN 0960-894X; Royaume-Uni; Da. 2001; Vol. 11; No. 16; Pp. 2137-2142
LA :	Anglais
EA :	The 3(2-adamantyl)pyrrolidines 8a g, 14 were synthesized and evaluated for activity against influenza A virus. The parent N H compound 14 was several times more active than amantadine against H₂N₂ and H₃N₂ influenza A virus. The combined use of NMR spectroscopy and computational chemistry showed that the conformation around the pyrrolidine-adamantyl carbon carbon bond is trans and the pyrrolidine heterocycle has an envelope conformation with C-2 out of the plane of the other ring atoms. N-Dialkylaminoethyl substitution of compound 14 resulted in the potent diamine analogues 8e,f,g. Interestingly, their lactam amine precursors were also active. Compounds 8e,f,g are the first adamantane derivatives, bearing two amine groups, reported to be active against influenza A virus.
CC :	002B02S05
FD :	Relation structure activité; Synthèse chimique; Composé tricyclique; Composé saturé; Hétérocycle azote; Diamine; Amine tertiaire; Antiviral; Virus grippal A; In vitro; Modélisation; Modèle moléculaire; Méthode dynamique moléculaire; Analyse conformationnelle; Adamamtane dérivé; Pyrrolidine(3-[2-adamantyl]-1-[2-(dialkylamino)ét hyl])
FG :	Influenzavirus A; Orthomyxoviridae; Virus
ED :	Structure activity relation; Chemical synthesis; Tricyclic compound; Saturated compound; Nitrogen heterocycle; Diamine; Tertiary amine; Antiviral; Influenza A virus; In vitro; Modeling; Molecular model; Molecular dynamics method; Conformational analysis
EG :	Influenzavirus A; Orthomyxoviridae; Virus
SD :	Relación estructura actividad; Síntesis química; Compuesto tricíclico; Compuesto saturado; Heterociclo nitrógeno; Diamina; Amina terciaria; Antiviral; Influenza A virus; In vitro; Modelización; Modelo molecular; Método dinámico molecular; Análisis conformacional
LO :	INIST-22446.354000095772720180
ID :	01-0423706

Links to Exploration step

Pascal:01-0423706

Le document en format XML

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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term>
<term>Chemical synthesis</term>
<term>Conformational analysis</term>
<term>Diamine</term>
<term>In vitro</term>
<term>Influenza A virus</term>
<term>Modeling</term>
<term>Molecular dynamics method</term>
<term>Molecular model</term>
<term>Nitrogen heterocycle</term>
<term>Saturated compound</term>
<term>Structure activity relation</term>
<term>Tertiary amine</term>
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<keywords scheme="Pascal" xml:lang="fr"><term>Relation structure activité</term>
<term>Synthèse chimique</term>
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<term>Composé saturé</term>
<term>Hétérocycle azote</term>
<term>Diamine</term>
<term>Amine tertiaire</term>
<term>Antiviral</term>
<term>Virus grippal A</term>
<term>In vitro</term>
<term>Modélisation</term>
<term>Modèle moléculaire</term>
<term>Méthode dynamique moléculaire</term>
<term>Analyse conformationnelle</term>
<term>Adamamtane dérivé</term>
<term>Pyrrolidine(3-[2-adamantyl]-1-[2-(dialkylamino)éthyl])</term>
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<front><div type="abstract" xml:lang="en">The 3(2-adamantyl)pyrrolidines 8a g, 14 were synthesized and evaluated for activity against influenza A virus. The parent N H compound 14 was several times more active than amantadine against H<sub>2</sub>
N<sub>2</sub>
 and H<sub>3</sub>
N<sub>2</sub>
 influenza A virus. The combined use of NMR spectroscopy and computational chemistry showed that the conformation around the pyrrolidine-adamantyl carbon carbon bond is trans and the pyrrolidine heterocycle has an envelope conformation with C-2 out of the plane of the other ring atoms. N-Dialkylaminoethyl substitution of compound 14 resulted in the potent diamine analogues 8e,f,g. Interestingly, their lactam amine precursors were also active. Compounds 8e,f,g are the first adamantane derivatives, bearing two amine groups, reported to be active against influenza A virus.</div>
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<fA11 i1="03" i2="1"><s1>KOLOCOURIS (Nicolas)</s1>
</fA11>
<fA11 i1="04" i2="1"><s1>FYTAS (George)</s1>
</fA11>
<fA11 i1="05" i2="1"><s1>FOSCOLOS (George B.)</s1>
</fA11>
<fA11 i1="06" i2="1"><s1>NEYTS (Johan)</s1>
</fA11>
<fA11 i1="07" i2="1"><s1>DE CLERCQ (Erik)</s1>
</fA11>
<fA14 i1="01"><s1>School of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Panepistimioupoli-Zografou</s1>
<s2>15771 Athens</s2>
<s3>GRC</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>4 aut.</sZ>
<sZ>5 aut.</sZ>
</fA14>
<fA14 i1="02"><s1>Rega Institute for Medical Research, Katholieke Universiteit Leuven</s1>
<s2>3000 Leuven</s2>
<s3>BEL</s3>
<sZ>6 aut.</sZ>
<sZ>7 aut.</sZ>
</fA14>
<fA20><s1>2137-2142</s1>
</fA20>
<fA21><s1>2001</s1>
</fA21>
<fA23 i1="01"><s0>ENG</s0>
</fA23>
<fA43 i1="01"><s1>INIST</s1>
<s2>22446</s2>
<s5>354000095772720180</s5>
</fA43>
<fA44><s0>0000</s0>
<s1>© 2001 INIST-CNRS. All rights reserved.</s1>
</fA44>
<fA47 i1="01" i2="1"><s0>01-0423706</s0>
</fA47>
<fA60><s1>P</s1>
</fA60>
<fA61><s0>A</s0>
</fA61>
<fA64 i1="01" i2="1"><s0>Bioorganic & medicinal chemistry letters</s0>
</fA64>
<fA66 i1="01"><s0>GBR</s0>
</fA66>
<fA99><s0>1/2 p. ref. et notes</s0>
</fA99>
<fC01 i1="01" l="ENG"><s0>The 3(2-adamantyl)pyrrolidines 8a g, 14 were synthesized and evaluated for activity against influenza A virus. The parent N H compound 14 was several times more active than amantadine against H<sub>2</sub>
N<sub>2</sub>
 and H<sub>3</sub>
N<sub>2</sub>
 influenza A virus. The combined use of NMR spectroscopy and computational chemistry showed that the conformation around the pyrrolidine-adamantyl carbon carbon bond is trans and the pyrrolidine heterocycle has an envelope conformation with C-2 out of the plane of the other ring atoms. N-Dialkylaminoethyl substitution of compound 14 resulted in the potent diamine analogues 8e,f,g. Interestingly, their lactam amine precursors were also active. Compounds 8e,f,g are the first adamantane derivatives, bearing two amine groups, reported to be active against influenza A virus.</s0>
</fC01>
<fC02 i1="01" i2="X"><s0>002B02S05</s0>
</fC02>
<fC03 i1="01" i2="X" l="FRE"><s0>Relation structure activité</s0>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="ENG"><s0>Structure activity relation</s0>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="SPA"><s0>Relación estructura actividad</s0>
<s5>01</s5>
</fC03>
<fC03 i1="02" i2="X" l="FRE"><s0>Synthèse chimique</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="ENG"><s0>Chemical synthesis</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="SPA"><s0>Síntesis química</s0>
<s5>02</s5>
</fC03>
<fC03 i1="03" i2="X" l="FRE"><s0>Composé tricyclique</s0>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="ENG"><s0>Tricyclic compound</s0>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="SPA"><s0>Compuesto tricíclico</s0>
<s5>03</s5>
</fC03>
<fC03 i1="04" i2="X" l="FRE"><s0>Composé saturé</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG"><s0>Saturated compound</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA"><s0>Compuesto saturado</s0>
<s5>04</s5>
</fC03>
<fC03 i1="05" i2="X" l="FRE"><s0>Hétérocycle azote</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="ENG"><s0>Nitrogen heterocycle</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="SPA"><s0>Heterociclo nitrógeno</s0>
<s5>05</s5>
</fC03>
<fC03 i1="06" i2="X" l="FRE"><s0>Diamine</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG"><s0>Diamine</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA"><s0>Diamina</s0>
<s5>06</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE"><s0>Amine tertiaire</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG"><s0>Tertiary amine</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA"><s0>Amina terciaria</s0>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Antiviral</s0>
<s5>09</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG"><s0>Antiviral</s0>
<s5>09</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Antiviral</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Virus grippal A</s0>
<s2>NW</s2>
<s5>10</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>Influenza A virus</s0>
<s2>NW</s2>
<s5>10</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Influenza A virus</s0>
<s2>NW</s2>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>In vitro</s0>
<s5>12</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>In vitro</s0>
<s5>12</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>In vitro</s0>
<s5>12</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE"><s0>Modélisation</s0>
<s5>17</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG"><s0>Modeling</s0>
<s5>17</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA"><s0>Modelización</s0>
<s5>17</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>Modèle moléculaire</s0>
<s5>18</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG"><s0>Molecular model</s0>
<s5>18</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA"><s0>Modelo molecular</s0>
<s5>18</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Méthode dynamique moléculaire</s0>
<s5>19</s5>
</fC03>
<fC03 i1="13" i2="X" l="ENG"><s0>Molecular dynamics method</s0>
<s5>19</s5>
</fC03>
<fC03 i1="13" i2="X" l="SPA"><s0>Método dinámico molecular</s0>
<s5>19</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>Analyse conformationnelle</s0>
<s5>20</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG"><s0>Conformational analysis</s0>
<s5>20</s5>
</fC03>
<fC03 i1="14" i2="X" l="SPA"><s0>Análisis conformacional</s0>
<s5>20</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE"><s0>Adamamtane dérivé</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>62</s5>
</fC03>
<fC03 i1="16" i2="X" l="FRE"><s0>Pyrrolidine(3-[2-adamantyl]-1-[2-(dialkylamino)éthyl])</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>63</s5>
</fC03>
<fC07 i1="01" i2="X" l="FRE"><s0>Influenzavirus A</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="01" i2="X" l="ENG"><s0>Influenzavirus A</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="01" i2="X" l="SPA"><s0>Influenzavirus A</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="FRE"><s0>Orthomyxoviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="ENG"><s0>Orthomyxoviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="SPA"><s0>Orthomyxoviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="FRE"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="ENG"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="SPA"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fN21><s1>295</s1>
</fN21>
</pA>
</standard>
<server><NO>PASCAL 01-0423706 INIST</NO>
<ET>Novel 3-(2-adamantyl)pyrrolidines with potent activity against influenza A virus : Identification of aminoadamantane derivatives bearing two pharmacophoric amine groups</ET>
<AU>STAMATIOU (George); KOLOCOURIS (Antonios); KOLOCOURIS (Nicolas); FYTAS (George); FOSCOLOS (George B.); NEYTS (Johan); DE CLERCQ (Erik)</AU>
<AF>School of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Panepistimioupoli-Zografou/15771 Athens/Grèce (1 aut., 2 aut., 3 aut., 4 aut., 5 aut.); Rega Institute for Medical Research, Katholieke Universiteit Leuven/3000 Leuven/Belgique (6 aut., 7 aut.)</AF>
<DT>Publication en série; Niveau analytique</DT>
<SO>Bioorganic & medicinal chemistry letters; ISSN 0960-894X; Royaume-Uni; Da. 2001; Vol. 11; No. 16; Pp. 2137-2142</SO>
<LA>Anglais</LA>
<EA>The 3(2-adamantyl)pyrrolidines 8a g, 14 were synthesized and evaluated for activity against influenza A virus. The parent N H compound 14 was several times more active than amantadine against H<sub>2</sub>
N<sub>2</sub>
 and H<sub>3</sub>
N<sub>2</sub>
 influenza A virus. The combined use of NMR spectroscopy and computational chemistry showed that the conformation around the pyrrolidine-adamantyl carbon carbon bond is trans and the pyrrolidine heterocycle has an envelope conformation with C-2 out of the plane of the other ring atoms. N-Dialkylaminoethyl substitution of compound 14 resulted in the potent diamine analogues 8e,f,g. Interestingly, their lactam amine precursors were also active. Compounds 8e,f,g are the first adamantane derivatives, bearing two amine groups, reported to be active against influenza A virus.</EA>
<CC>002B02S05</CC>
<FD>Relation structure activité; Synthèse chimique; Composé tricyclique; Composé saturé; Hétérocycle azote; Diamine; Amine tertiaire; Antiviral; Virus grippal A; In vitro; Modélisation; Modèle moléculaire; Méthode dynamique moléculaire; Analyse conformationnelle; Adamamtane dérivé; Pyrrolidine(3-[2-adamantyl]-1-[2-(dialkylamino)ét hyl])</FD>
<FG>Influenzavirus A; Orthomyxoviridae; Virus</FG>
<ED>Structure activity relation; Chemical synthesis; Tricyclic compound; Saturated compound; Nitrogen heterocycle; Diamine; Tertiary amine; Antiviral; Influenza A virus; In vitro; Modeling; Molecular model; Molecular dynamics method; Conformational analysis</ED>
<EG>Influenzavirus A; Orthomyxoviridae; Virus</EG>
<SD>Relación estructura actividad; Síntesis química; Compuesto tricíclico; Compuesto saturado; Heterociclo nitrógeno; Diamina; Amina terciaria; Antiviral; Influenza A virus; In vitro; Modelización; Modelo molecular; Método dinámico molecular; Análisis conformacional</SD>
<LO>INIST-22446.354000095772720180</LO>
<ID>01-0423706</ID>
</server>
</inist>
</record>

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Novel 3-(2-adamantyl)pyrrolidines with potent activity against influenza A virus : Identification of aminoadamantane derivatives bearing two pharmacophoric amine groups

Novel 3-(2-adamantyl)pyrrolidines with potent activity against influenza A virus : Identification of aminoadamantane derivatives bearing two pharmacophoric amine groups

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