Synthesis and Antiviral Activity Evaluation of Some New Aminoadamantane Derivatives. 2
Identifieur interne : 001C09 ( Main/Exploration ); précédent : 001C08; suivant : 001C10Synthesis and Antiviral Activity Evaluation of Some New Aminoadamantane Derivatives. 2
Auteurs : Nicolas Kolocouris [Belgique] ; Antonios Kolocouris [Belgique] ; George B. Foscolos [Belgique] ; George Fytas [Belgique] ; Johan Neyts [Belgique] ; Elisabeth Padalko [Belgique] ; Jan Balzarini [Belgique] ; Robert Snoeck [Belgique] ; Graciela Andrei [Belgique] ; Erik De Clercq [Belgique]Source :
- Journal of Medicinal Chemistry [ 0022-2623 ] ; 1996.
Descripteurs français
- KwdFr :
- Adamantane (), Adamantane (analogues et dérivés), Adamantane (pharmacologie), Adamantane (synthèse chimique), Animaux, Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Chiens, Cytomegalovirus (), Entérovirus humain B (), Herpèsvirus humain de type 3 (), Humains, Indicateurs et réactifs, Lignée cellulaire, Orthomyxoviridae (), Relation structure-activité, Reoviridae (), Structure moléculaire, Tests de sensibilité microbienne, VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (), VIH-2 (Virus de l'Immunodéficience Humaine de type 2) (), Virus Sindbis (), Virus de la forêt de Semliki (), Virus de la stomatite vésiculeuse de type Indiana (), Virus de la vaccine ().
- MESH :
- analogues et dérivés : Adamantane.
- pharmacologie : Adamantane, Antiviraux.
- synthèse chimique : Adamantane, Antiviraux.
- Adamantane, Animaux, Antiviraux, Chiens, Cytomegalovirus, Entérovirus humain B, Herpèsvirus humain de type 3, Humains, Indicateurs et réactifs, Lignée cellulaire, Orthomyxoviridae, Relation structure-activité, Reoviridae, Structure moléculaire, Tests de sensibilité microbienne, VIH-1 (Virus de l'Immunodéficience Humaine de type 1), VIH-2 (Virus de l'Immunodéficience Humaine de type 2), Virus Sindbis, Virus de la forêt de Semliki, Virus de la stomatite vésiculeuse de type Indiana, Virus de la vaccine.
- Pascal (Inist)
- Adamantane(1-[1-(dialkylamino)cyclopentyl]), Adamantane(1-[2-alkylpyrrolidin-2-yl]), Amine tertiaire, Antiviral, Hétérocycle azote, Hétérocycle oxygène azote, In vitro, Influenzavirus A, Relation structure activité, Spirane, Spiro[adamantane-1:2p-pipéridine](1p-alkyl), Spiro[adamantane-1:3p-morpholine](4p-alkyl), Synthèse chimique.
English descriptors
- KwdEn :
- Adamantane (analogs & derivatives), Adamantane (chemical synthesis), Adamantane (chemistry), Adamantane (pharmacology), Animals, Antiviral, Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cell Line, Chemical synthesis, Chlorocebus aethiops, Cytomegalovirus (drug effects), Dogs, Enterovirus B, Human (drug effects), HIV-1 (drug effects), HIV-2 (drug effects), Herpesvirus 3, Human (drug effects), Humans, In vitro, Indicators and Reagents, Influenzavirus A, Microbial Sensitivity Tests, Molecular Structure, Nitrogen heterocycle, Orthomyxoviridae (drug effects), Oxygen nitrogen heterocycle, Reoviridae (drug effects), Semliki forest virus (drug effects), Sindbis Virus (drug effects), Spiran, Structure activity relation, Structure-Activity Relationship, Tertiary amine, Vaccinia virus (drug effects), Vesicular stomatitis Indiana virus (drug effects).
- MESH :
- chemical , analogs & derivatives : Adamantane.
- chemical , chemical synthesis : Adamantane, Antiviral Agents.
- chemical , chemistry : Adamantane, Antiviral Agents.
- chemical , pharmacology : Adamantane, Antiviral Agents.
- drug effects : Cytomegalovirus, Enterovirus B, Human, HIV-1, HIV-2, Herpesvirus 3, Human, Orthomyxoviridae, Reoviridae, Semliki forest virus, Sindbis Virus, Vaccinia virus, Vesicular stomatitis Indiana virus.
- Animals, Cell Line, Chlorocebus aethiops, Dogs, Humans, Indicators and Reagents, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.
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.
Url:
DOI: 10.1021/jm950891z
Affiliations:
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Le document en format XML
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Med. Chem.</title><idno type="ISSN">0022-2623</idno><idno type="eISSN">1520-4804</idno><imprint><publisher>American Chemical Society</publisher><date type="e-published" when="1996-08-16">1996</date><date when="1996-08-16">1996</date><biblScope unit="vol">39</biblScope><biblScope unit="issue">17</biblScope><biblScope unit="page" from="3307">3307</biblScope><biblScope unit="page" to="3318">3318</biblScope></imprint><idno type="ISSN">0022-2623</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0022-2623</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Adamantane (analogs & derivatives)</term><term>Adamantane (chemical synthesis)</term><term>Adamantane (chemistry)</term><term>Adamantane (pharmacology)</term><term>Animals</term><term>Antiviral</term><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Cell Line</term><term>Chemical synthesis</term><term>Chlorocebus aethiops</term><term>Cytomegalovirus (drug effects)</term><term>Dogs</term><term>Enterovirus B, Human (drug effects)</term><term>HIV-1 (drug effects)</term><term>HIV-2 (drug effects)</term><term>Herpesvirus 3, Human (drug effects)</term><term>Humans</term><term>In vitro</term><term>Indicators and Reagents</term><term>Influenzavirus A</term><term>Microbial Sensitivity Tests</term><term>Molecular Structure</term><term>Nitrogen heterocycle</term><term>Orthomyxoviridae (drug effects)</term><term>Oxygen nitrogen heterocycle</term><term>Reoviridae (drug effects)</term><term>Semliki forest virus (drug effects)</term><term>Sindbis Virus (drug effects)</term><term>Spiran</term><term>Structure activity relation</term><term>Structure-Activity Relationship</term><term>Tertiary amine</term><term>Vaccinia virus (drug effects)</term><term>Vesicular stomatitis Indiana virus (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Adamantane ()</term><term>Adamantane (analogues et dérivés)</term><term>Adamantane (pharmacologie)</term><term>Adamantane (synthèse chimique)</term><term>Animaux</term><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Chiens</term><term>Cytomegalovirus ()</term><term>Entérovirus humain B ()</term><term>Herpèsvirus humain de type 3 ()</term><term>Humains</term><term>Indicateurs et réactifs</term><term>Lignée cellulaire</term><term>Orthomyxoviridae ()</term><term>Relation structure-activité</term><term>Reoviridae ()</term><term>Structure moléculaire</term><term>Tests de sensibilité microbienne</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term><term>VIH-2 (Virus de l'Immunodéficience Humaine de type 2) ()</term><term>Virus Sindbis ()</term><term>Virus de la forêt de Semliki ()</term><term>Virus de la stomatite vésiculeuse de type Indiana ()</term><term>Virus de la vaccine ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Adamantane</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Adamantane</term><term>Antiviral Agents</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Adamantane</term><term>Antiviral Agents</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Adamantane</term><term>Antiviral Agents</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Adamantane</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Cytomegalovirus</term><term>Enterovirus B, Human</term><term>HIV-1</term><term>HIV-2</term><term>Herpesvirus 3, Human</term><term>Orthomyxoviridae</term><term>Reoviridae</term><term>Semliki forest virus</term><term>Sindbis Virus</term><term>Vaccinia virus</term><term>Vesicular stomatitis Indiana virus</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Adamantane</term><term>Antiviraux</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Adamantane</term><term>Antiviraux</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Cell Line</term><term>Chlorocebus aethiops</term><term>Dogs</term><term>Humans</term><term>Indicators and Reagents</term><term>Microbial Sensitivity Tests</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Adamantane</term><term>Animaux</term><term>Antiviraux</term><term>Chiens</term><term>Cytomegalovirus</term><term>Entérovirus humain B</term><term>Herpèsvirus humain de type 3</term><term>Humains</term><term>Indicateurs et réactifs</term><term>Lignée cellulaire</term><term>Orthomyxoviridae</term><term>Relation structure-activité</term><term>Reoviridae</term><term>Structure moléculaire</term><term>Tests de sensibilité microbienne</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term><term>VIH-2 (Virus de l'Immunodéficience Humaine de type 2)</term><term>Virus Sindbis</term><term>Virus de la forêt de Semliki</term><term>Virus de la stomatite vésiculeuse de type Indiana</term><term>Virus de la vaccine</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Adamantane(1-[1-(dialkylamino)cyclopentyl])</term><term>Adamantane(1-[2-alkylpyrrolidin-2-yl])</term><term>Amine tertiaire</term><term>Antiviral</term><term>Hétérocycle azote</term><term>Hétérocycle oxygène azote</term><term>In vitro</term><term>Influenzavirus A</term><term>Relation structure activité</term><term>Spirane</term><term>Spiro[adamantane-1:2p-pipéridine](1p-alkyl)</term><term>Spiro[adamantane-1:3p-morpholine](4p-alkyl)</term><term>Synthèse chimique</term></keywords></textClass></profileDesc></teiHeader><front><div type="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.</div></front></TEI><affiliations><list><country><li>Belgique</li></country></list><tree><country name="Belgique"><noRegion><name sortKey="Kolocouris, Nicolas" sort="Kolocouris, Nicolas" uniqKey="Kolocouris N" first="Nicolas" last="Kolocouris">Nicolas Kolocouris</name></noRegion><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><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="Neyts, Johan" sort="Neyts, Johan" uniqKey="Neyts J" first="Johan" last="Neyts">Johan Neyts</name><name sortKey="Padalko, Elisabeth" sort="Padalko, Elisabeth" uniqKey="Padalko E" first="Elisabeth" last="Padalko">Elisabeth Padalko</name><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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