Aminocyclopropanes as precursors of endoperoxides with antimalarial activity
Identifieur interne : 001654 ( Main/Exploration ); précédent : 001653; suivant : 001655Aminocyclopropanes as precursors of endoperoxides with antimalarial activity
Auteurs : Claire Madelaine [France] ; Olivier Buriez [France] ; Benot Crousse [France] ; Isabelle Florent [France] ; Philippe Grellier [France] ; Pascal Retailleau [France] ; Yvan Six [France]Source :
- Organic & Biomolecular Chemistry [ 1477-0520 ] ; 2010.
English descriptors
- Teeft :
- Abxy system, Abxyz system, Alumina, Amide, Aminocyclopropanation reactions, Aminocyclopropane, Aminocyclopropanes, Angew, Anodic compartment, Bicyclic, Bicyclic aminocyclopropanes, Biomol, Cdcl3, Characteristic signals, Chcf3, Chem, Colourless, Crude product, Crude products, Cyclic, Cyclic voltammetry, Diastereoisomeric, Diastereoisomeric aminocyclopropane products, Diastereoisomeric endoperoxide products, Diastereoisomers, Diethyl ether, Double bond, Endoperoxide, Endoperoxides, Equiv, Falciparum, Flash chromatography, General procedure, Hco2, Hco2 hco2, Hplc, Intramolecular, Intramolecular meijere reactions, Meijere, Mmol, Neutral alumina, Nitrogen atom, Plasmodium, Plasmodium falciparum, Potential values, Preparative hplc, Retention time, Royal society, Small amount, Substituent, Voltammetry.
Abstract
This contribution describes the synthesis of several novel bicyclic -amino endoperoxides, including CF3-substituted compounds, prepared by the aerobic electrochemical oxidation of a family of bicyclic aminocyclopropanes. These, in turn, are readily synthesised by a titanium-mediated intramolecular cyclopropanation process (Kulinkovichde Meijere reaction), starting from N-alkenyl amides that contain a vic-disubstituted double bond, with high diastereoselectivity. An evaluation of the biological activities of several of the molecules produced, against the parasite Plasmodium falciparum, is also presented.
Url:
DOI: 10.1039/c0ob00308e
Affiliations:
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first="Isabelle" last="Florent">Isabelle Florent</name><affiliation wicri:level="3"><country xml:lang="fr">France</country><wicri:regionArea>Musum National dHistoire Naturelle, FRE 3206 CNRS, 61 rue Buffon, 75231 Paris Cedex 05</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Paris</settlement></placeName></affiliation></author><author wicri:is="90%"><name sortKey="Grellier, Philippe" sort="Grellier, Philippe" uniqKey="Grellier P" first="Philippe" last="Grellier">Philippe Grellier</name><affiliation wicri:level="3"><country xml:lang="fr">France</country><wicri:regionArea>Musum National dHistoire Naturelle, FRE 3206 CNRS, 61 rue Buffon, 75231 Paris Cedex 05</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Paris</settlement></placeName></affiliation></author><author wicri:is="90%"><name sortKey="Retailleau, Pascal" sort="Retailleau, Pascal" uniqKey="Retailleau P" first="Pascal" last="Retailleau">Pascal Retailleau</name><affiliation wicri:level="3"><country xml:lang="fr">France</country><wicri:regionArea>Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Gif-sur-Yvette</settlement></placeName></affiliation></author><author wicri:is="90%"><name sortKey="Six, Yvan" sort="Six, Yvan" uniqKey="Six Y" first="Yvan" last="Six">Yvan Six</name><affiliation wicri:level="3"><country xml:lang="fr">France</country><wicri:regionArea>Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Gif-sur-Yvette</settlement></placeName></affiliation><affiliation wicri:level="3"><country xml:lang="fr">France</country><wicri:regionArea>Present address: Dpartement de Chimie, UMR 7652, CNRS/Ecole Polytechnique, 91128 Palaiseau</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Palaiseau</settlement></placeName></affiliation><affiliation wicri:level="1"><country wicri:rule="url">France</country></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="2010">2010</date><biblScope unit="volume">8</biblScope><biblScope unit="issue">24</biblScope><biblScope unit="page" from="5591">5591</biblScope><biblScope unit="page" to="5601">5601</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>Abxy system</term><term>Abxyz system</term><term>Alumina</term><term>Amide</term><term>Aminocyclopropanation reactions</term><term>Aminocyclopropane</term><term>Aminocyclopropanes</term><term>Angew</term><term>Anodic compartment</term><term>Bicyclic</term><term>Bicyclic aminocyclopropanes</term><term>Biomol</term><term>Cdcl3</term><term>Characteristic signals</term><term>Chcf3</term><term>Chem</term><term>Colourless</term><term>Crude product</term><term>Crude products</term><term>Cyclic</term><term>Cyclic voltammetry</term><term>Diastereoisomeric</term><term>Diastereoisomeric aminocyclopropane products</term><term>Diastereoisomeric endoperoxide products</term><term>Diastereoisomers</term><term>Diethyl ether</term><term>Double bond</term><term>Endoperoxide</term><term>Endoperoxides</term><term>Equiv</term><term>Falciparum</term><term>Flash chromatography</term><term>General procedure</term><term>Hco2</term><term>Hco2 hco2</term><term>Hplc</term><term>Intramolecular</term><term>Intramolecular meijere reactions</term><term>Meijere</term><term>Mmol</term><term>Neutral alumina</term><term>Nitrogen atom</term><term>Plasmodium</term><term>Plasmodium falciparum</term><term>Potential values</term><term>Preparative hplc</term><term>Retention time</term><term>Royal society</term><term>Small amount</term><term>Substituent</term><term>Voltammetry</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract">This contribution describes the synthesis of several novel bicyclic -amino endoperoxides, including CF3-substituted compounds, prepared by the aerobic electrochemical oxidation of a family of bicyclic aminocyclopropanes. These, in turn, are readily synthesised by a titanium-mediated intramolecular cyclopropanation process (Kulinkovichde Meijere reaction), starting from N-alkenyl amides that contain a vic-disubstituted double bond, with high diastereoselectivity. An evaluation of the biological activities of several of the molecules produced, against the parasite Plasmodium falciparum, is also presented.</div></front></TEI><affiliations><list><country><li>France</li></country><region><li>Île-de-France</li></region><settlement><li>Chtenay-Malabry</li><li>Gif-sur-Yvette</li><li>Palaiseau</li><li>Paris</li></settlement></list><tree><country name="France"><region name="Île-de-France"><name sortKey="Madelaine, Claire" sort="Madelaine, Claire" uniqKey="Madelaine C" first="Claire" last="Madelaine">Claire Madelaine</name></region><name sortKey="Buriez, Olivier" sort="Buriez, Olivier" uniqKey="Buriez O" first="Olivier" last="Buriez">Olivier Buriez</name><name sortKey="Crousse, Benot" sort="Crousse, Benot" uniqKey="Crousse B" first="Benot" last="Crousse">Benot Crousse</name><name sortKey="Florent, Isabelle" sort="Florent, Isabelle" uniqKey="Florent I" first="Isabelle" last="Florent">Isabelle Florent</name><name sortKey="Grellier, Philippe" sort="Grellier, Philippe" uniqKey="Grellier P" first="Philippe" last="Grellier">Philippe Grellier</name><name sortKey="Retailleau, Pascal" sort="Retailleau, Pascal" uniqKey="Retailleau P" first="Pascal" last="Retailleau">Pascal Retailleau</name><name sortKey="Six, Yvan" sort="Six, Yvan" uniqKey="Six Y" first="Yvan" last="Six">Yvan Six</name><name sortKey="Six, Yvan" sort="Six, Yvan" uniqKey="Six Y" first="Yvan" last="Six">Yvan Six</name><name sortKey="Six, Yvan" sort="Six, Yvan" uniqKey="Six Y" first="Yvan" last="Six">Yvan Six</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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