Design and synthesis of bioactive 1,2-annulated adamantane derivatives
Identifieur interne : 001298 ( Main/Exploration ); précédent : 001297; suivant : 001299Design and synthesis of bioactive 1,2-annulated adamantane derivatives
Auteurs : Grigoris Zoidis [Grèce] ; Andrew Tsotinis [Grèce] ; Nicolas Kolocouris [Grèce] ; John M. Kelly [Royaume-Uni] ; S. Radhika Prathalingam [Royaume-Uni] ; Lieve Naesens [Belgique] ; Erik De Clercq [Belgique]Source :
- Organic & Biomolecular Chemistry [ 1477-0520 ] ; 2008.
English descriptors
- Teeft :
- Amantadine, Ambient temperature, Amine, Aminoadamantane, Aminoadamantane derivatives, Anal, Biomol, Bloodstream form, Brucei, Calcd, Cdcl3, Chem, Clercq, Column chromatography, Derivative, Ester, Ethanolic solution, Ether, Etoh, Fytas, Hydrochloride salt, Kolocouris, Lactam, Lialh4, Ltered, Mmax, Mmol, Oily product, Organic phase, Oxime, Oxime ester, Pyrrolidine, Pyrrolidines, Rimantadine, Room temperature, Royal society, Trypanocidal, Trypanocidal activity, Virus activity, Vmax, Xylene.
Abstract
Adamantanopyrrolidines 8, 9 and 10, adamantanopyrrolidines 16 and 18, adamantanoxazolone 20, adamantanopyrazolone 23, adamantanopyrazolothione 24 and adamantanocyclopentanamine 32 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated. Pyrrolidine 16 proved to be the most active of the compounds tested against influenza A virus, being 4-fold more active than amantadine, equipotent to rimantadine and 19-fold more potent than ribavirin. Oxazolone 20 showed significant trypanocidal activity against bloodstream forms of the African trypanosome, Trypanosoma brucei, being approximately 3 times more potent than rimantadine and almost 50-fold more active than amantadine.
Url:
DOI: 10.1039/b804907f
Affiliations:
- Belgique, Grèce, Royaume-Uni
- Angleterre, Attique (région), Grand Londres, Province du Brabant flamand, Région flamande
- Athènes, Londres, Louvain
- Katholieke Universiteit Leuven
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Le document en format XML
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Kelly</name><affiliation wicri:level="3"><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>London School of Hygiene and Tropical Medicine, Department of Infectious and Tropical Diseases, WC1E 7HT, Keppel Street, London</wicri:regionArea><placeName><settlement type="city">Londres</settlement><region type="country">Angleterre</region><region type="région" nuts="1">Grand Londres</region></placeName></affiliation></author><author wicri:is="90%"><name sortKey="Prathalingam, S Radhika" sort="Prathalingam, S Radhika" uniqKey="Prathalingam S" first="S. Radhika" last="Prathalingam">S. Radhika Prathalingam</name><affiliation wicri:level="3"><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>London School of Hygiene and Tropical Medicine, Department of Infectious and Tropical Diseases, WC1E 7HT, Keppel Street, London</wicri:regionArea><placeName><settlement type="city">Londres</settlement><region type="country">Angleterre</region><region type="région" nuts="1">Grand Londres</region></placeName></affiliation></author><author wicri:is="90%"><name sortKey="Naesens, Lieve" sort="Naesens, Lieve" uniqKey="Naesens L" first="Lieve" last="Naesens">Lieve Naesens</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute, Department of Microbiology and Immunology, Katholieke Universiteit Leuven, 3000 Leuven, Minderbroedersstraat 10</wicri:regionArea><orgName type="university">Katholieke Universiteit Leuven</orgName><placeName><settlement type="city">Louvain</settlement><region>Région flamande</region><region type="district" nuts="2">Province du Brabant flamand</region></placeName></affiliation></author><author wicri:is="90%"><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><affiliation wicri:level="4"><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute, Department of Microbiology and Immunology, Katholieke Universiteit Leuven, 3000 Leuven, Minderbroedersstraat 10</wicri:regionArea><orgName type="university">Katholieke Universiteit Leuven</orgName><placeName><settlement type="city">Louvain</settlement><region>Région flamande</region><region type="district" nuts="2">Province du Brabant flamand</region></placeName></affiliation></author></analytic><monogr></monogr><series><title level="j">Organic & Biomolecular Chemistry</title><title level="j" type="abbrev">Org. Biomol. Chem.</title><idno type="ISSN">1477-0520</idno><idno type="eISSN">1477-0539</idno><imprint><publisher>The Royal Society of Chemistry.</publisher><date type="published" when="2008">2008</date><biblScope unit="volume">6</biblScope><biblScope unit="issue">17</biblScope><biblScope unit="page" from="3177">3177</biblScope><biblScope unit="page" to="3185">3185</biblScope></imprint><idno type="ISSN">1477-0520</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1477-0520</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="Teeft" xml:lang="en"><term>Amantadine</term><term>Ambient temperature</term><term>Amine</term><term>Aminoadamantane</term><term>Aminoadamantane derivatives</term><term>Anal</term><term>Biomol</term><term>Bloodstream form</term><term>Brucei</term><term>Calcd</term><term>Cdcl3</term><term>Chem</term><term>Clercq</term><term>Column chromatography</term><term>Derivative</term><term>Ester</term><term>Ethanolic solution</term><term>Ether</term><term>Etoh</term><term>Fytas</term><term>Hydrochloride salt</term><term>Kolocouris</term><term>Lactam</term><term>Lialh4</term><term>Ltered</term><term>Mmax</term><term>Mmol</term><term>Oily product</term><term>Organic phase</term><term>Oxime</term><term>Oxime ester</term><term>Pyrrolidine</term><term>Pyrrolidines</term><term>Rimantadine</term><term>Room temperature</term><term>Royal society</term><term>Trypanocidal</term><term>Trypanocidal activity</term><term>Virus activity</term><term>Vmax</term><term>Xylene</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract">Adamantanopyrrolidines 8, 9 and 10, adamantanopyrrolidines 16 and 18, adamantanoxazolone 20, adamantanopyrazolone 23, adamantanopyrazolothione 24 and adamantanocyclopentanamine 32 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated. Pyrrolidine 16 proved to be the most active of the compounds tested against influenza A virus, being 4-fold more active than amantadine, equipotent to rimantadine and 19-fold more potent than ribavirin. Oxazolone 20 showed significant trypanocidal activity against bloodstream forms of the African trypanosome, Trypanosoma brucei, being approximately 3 times more potent than rimantadine and almost 50-fold more active than amantadine.</div></front></TEI><affiliations><list><country><li>Belgique</li><li>Grèce</li><li>Royaume-Uni</li></country><region><li>Angleterre</li><li>Attique (région)</li><li>Grand Londres</li><li>Province du Brabant flamand</li><li>Région flamande</li></region><settlement><li>Athènes</li><li>Londres</li><li>Louvain</li></settlement><orgName><li>Katholieke Universiteit Leuven</li></orgName></list><tree><country name="Grèce"><region name="Attique (région)"><name sortKey="Zoidis, Grigoris" sort="Zoidis, Grigoris" uniqKey="Zoidis G" first="Grigoris" last="Zoidis">Grigoris Zoidis</name></region><name sortKey="Kolocouris, Nicolas" sort="Kolocouris, Nicolas" uniqKey="Kolocouris N" first="Nicolas" last="Kolocouris">Nicolas Kolocouris</name><name sortKey="Tsotinis, Andrew" sort="Tsotinis, Andrew" uniqKey="Tsotinis A" first="Andrew" last="Tsotinis">Andrew Tsotinis</name></country><country name="Royaume-Uni"><region name="Angleterre"><name sortKey="Kelly, John M" sort="Kelly, John M" uniqKey="Kelly J" first="John M." last="Kelly">John M. Kelly</name></region><name sortKey="Prathalingam, S Radhika" sort="Prathalingam, S Radhika" uniqKey="Prathalingam S" first="S. Radhika" last="Prathalingam">S. Radhika Prathalingam</name></country><country name="Belgique"><region name="Région flamande"><name sortKey="Naesens, Lieve" sort="Naesens, Lieve" uniqKey="Naesens L" first="Lieve" last="Naesens">Lieve Naesens</name></region><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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