H2N2V1, Main, Merge, bibRecord, 001D59

Synthesis and antiviral activity evaluation of some new aminoadamantane derivatives. 2

Identifieur interne : 001D59 ( Main/Merge ); précédent : 001D58; suivant : 001D60

Synthesis and antiviral activity evaluation of some new aminoadamantane derivatives. 2

Auteurs : N. Kolocouris [Grèce] ; A. Kolocouris [Grèce] ; G. B. Foscolos [Grèce] ; G. Fytas [Grèce] ; J. Neyts [Belgique] ; E. Padalko [Belgique] ; J. Balzarini [Belgique] ; R. Snoeck [Belgique] ; G. Andrei [Belgique] ; E. De Clercq [Belgique]

Source :

Journal of medicinal chemistry [ 0022-2623 ] ; 1996.

RBID : Pascal:96-0394681

Descripteurs français

Pascal (Inist)
- Relation structure activité, Antiviral, In vitro, Influenzavirus A, Synthèse chimique, Spirane, Hétérocycle azote, Hétérocycle oxygène azote, Amine tertiaire, Spiro[adamantane-1:2p-pipéridine](1p-alkyl), Spiro[adamantane-1:3p-morpholine](4p-alkyl), Adamantane(1-[2-alkylpyrrolidin-2-yl]), Adamantane(1-[1-(dialkylamino)cyclopentyl]).

English descriptors

KwdEn :
- Antiviral, Chemical synthesis, In vitro, Influenzavirus A, Nitrogen heterocycle, Oxygen nitrogen heterocycle, Spiran, Structure activity relation, Tertiary amine.

Abstract

The synthesis of some new aminoadamantane derivatives is described. The new compounds were evaluated against a wide range of viruses [influenza A H1N1, influenza A H2N2, influenza A H3N2, influenza B, parainfluenza 3, herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2), thymidine kinase-deficient (TK^-) HSV-1, vaccinia, vesicular stomatitis, polio 1, Coxsackie B4, Sindbis, Semliki forest, Reo 1, varicella-zoster virus (VZV), TK^- VZV, human cytomegalovirus (HCMV), and human immunodeficiency virus type 1 (HIV-1) and type 2 (HIV-2)]. Some of them proved markedly active against the influenza A H2N2 (compounds 4a,b, 5a, 6a, and 7a), H3N2 (compounds 5a, 6a, and 7a), and H1N1 (compounds 4b,c and 6d). Since compounds 5a, 6a, and 7a, amantadine, and rimantadine showed the same comparative pattern of potency against influenza strains H2N2, H3N2, and B, it may postulated that they act according to a similar mechanism, with regard to their "amine" effect, on the M2 ion channel of influenza A (H1N1, H2N2, or H3N2). In general, no significant activity was noted with any of the new compounds against any of the other viruses tested, making their activity against influenza virus more specific and striking. Borderline activity was noted with some of the compounds (4b,c, 5a-c, and 8a) against HIV-1.

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Pascal:96-0394681

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>In vitro</term>
<term>Influenzavirus A</term>
<term>Nitrogen heterocycle</term>
<term>Oxygen nitrogen heterocycle</term>
<term>Spiran</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>Antiviral</term>
<term>In vitro</term>
<term>Influenzavirus A</term>
<term>Synthèse chimique</term>
<term>Spirane</term>
<term>Hétérocycle azote</term>
<term>Hétérocycle oxygène azote</term>
<term>Amine tertiaire</term>
<term>Spiro[adamantane-1:2p-pipéridine](1p-alkyl)</term>
<term>Spiro[adamantane-1:3p-morpholine](4p-alkyl)</term>
<term>Adamantane(1-[2-alkylpyrrolidin-2-yl])</term>
<term>Adamantane(1-[1-(dialkylamino)cyclopentyl])</term>
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<front><div type="abstract" xml:lang="en">The synthesis of some new aminoadamantane derivatives is described. The new compounds were evaluated against a wide range of viruses [influenza A H1N1, influenza A H2N2, influenza A H3N2, influenza B, parainfluenza 3, herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2), thymidine kinase-deficient (TK<sup>-</sup>
) HSV-1, vaccinia, vesicular stomatitis, polio 1, Coxsackie B4, Sindbis, Semliki forest, Reo 1, varicella-zoster virus (VZV), TK<sup>-</sup>
 VZV, human cytomegalovirus (HCMV), and human immunodeficiency virus type 1 (HIV-1) and type 2 (HIV-2)]. Some of them proved markedly active against the influenza A H2N2 (compounds 4a,b, 5a, 6a, and 7a), H3N2 (compounds 5a, 6a, and 7a), and H1N1 (compounds 4b,c and 6d). Since compounds 5a, 6a, and 7a, amantadine, and rimantadine showed the same comparative pattern of potency against influenza strains H2N2, H3N2, and B, it may postulated that they act according to a similar mechanism, with regard to their "amine" effect, on the M2 ion channel of influenza A (H1N1, H2N2, or H3N2). In general, no significant activity was noted with any of the new compounds against any of the other viruses tested, making their activity against influenza virus more specific and striking. Borderline activity was noted with some of the compounds (4b,c, 5a-c, and 8a) against HIV-1.</div>
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<orgName><li>Katholieke Universiteit Leuven</li>
</orgName>
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<tree><country name="Grèce"><region name="Attique (région)"><name sortKey="Kolocouris, N" sort="Kolocouris, N" uniqKey="Kolocouris N" first="N." last="Kolocouris">N. Kolocouris</name>
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<name sortKey="Fytas, G" sort="Fytas, G" uniqKey="Fytas G" first="G." last="Fytas">G. Fytas</name>
<name sortKey="Kolocouris, A" sort="Kolocouris, A" uniqKey="Kolocouris A" first="A." last="Kolocouris">A. Kolocouris</name>
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<country name="Belgique"><region name="Province du Brabant flamand"><name sortKey="Neyts, J" sort="Neyts, J" uniqKey="Neyts J" first="J." last="Neyts">J. Neyts</name>
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<name sortKey="Andrei, G" sort="Andrei, G" uniqKey="Andrei G" first="G." last="Andrei">G. Andrei</name>
<name sortKey="Balzarini, J" sort="Balzarini, J" uniqKey="Balzarini J" first="J." last="Balzarini">J. Balzarini</name>
<name sortKey="De Clercq, E" sort="De Clercq, E" uniqKey="De Clercq E" first="E." last="De Clercq">E. De Clercq</name>
<name sortKey="Padalko, E" sort="Padalko, E" uniqKey="Padalko E" first="E." last="Padalko">E. Padalko</name>
<name sortKey="Snoeck, R" sort="Snoeck, R" uniqKey="Snoeck R" first="R." last="Snoeck">R. Snoeck</name>
</country>
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Synthesis and antiviral activity evaluation of some new aminoadamantane derivatives. 2

Synthesis and antiviral activity evaluation of some new aminoadamantane derivatives. 2

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