Design and Synthesis of Hydroxyferroquine Derivatives with Antimalarial and Antiviral Activities
Identifieur interne : 004085 ( Main/Curation ); précédent : 004084; suivant : 004086Design and Synthesis of Hydroxyferroquine Derivatives with Antimalarial and Antiviral Activities
Auteurs : Christophe Biot [Belgique, France] ; Wassim Daher [Belgique] ; Natascha Chavain [Belgique] ; Thierry Fandeur [Belgique] ; Jamal Khalife [Belgique] ; Daniel Dive [Belgique] ; Erik De Clercq [Belgique]Source :
- Journal of Medicinal Chemistry [ 0022-2623 ] ; 2006.
Descripteurs français
- KwdFr :
- Animaux, Antipaludiques (), Antipaludiques (pharmacologie), Antipaludiques (synthèse chimique), Antipaludiques (toxicité), Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Antiviraux (toxicité), Composés du fer II (), Composés du fer II (pharmacologie), Composés du fer II (synthèse chimique), Composés du fer II (toxicité), Conception de médicament, Plasmodium falciparum (), Quinoléines (), Quinoléines (pharmacologie), Quinoléines (synthèse chimique), Quinoléines (toxicité), Structure moléculaire, VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (), Virus du SRAS ().
- MESH :
- pharmacologie : Antipaludiques, Antiviraux, Composés du fer II, Quinoléines.
- synthèse chimique : Antipaludiques, Antiviraux, Composés du fer II, Quinoléines.
- toxicité : Antipaludiques, Antiviraux, Composés du fer II, Quinoléines.
- Animaux, Antipaludiques, Antiviraux, Composés du fer II, Conception de médicament, Plasmodium falciparum, Quinoléines, Structure moléculaire, VIH-1 (Virus de l'Immunodéficience Humaine de type 1), Virus du SRAS.
- Pascal (Inist)
- Activité biologique, Alcool primaire, Aminoalcool, Antipaludique, Antiparasitaire, Antiprotozoaire, Antiviral, Coronavirus, Ethanolamine(N-[(2-[([7-chloro-4-quinolyl]amino)méthyl]ferrocényl)méthyl]), Ethanolamine(N-[(2-[([7-chloro-4-quinolyl]amino)méthyl]ferrocényl)méthyl]-N-méthyl), Ethanolamine(N-[(2-[([7-chloro-4-quinolyl]amino)méthyl]ferrocényl)méthyl]-N-éthyl), Ferrocène dérivé, In vitro, Métallocène, Plasmodium falciparum, Quinoléine dérivé, Synthèse chimique.
English descriptors
- KwdEn :
- Aminoalcohol, Animals, Antimalarial, Antimalarials (chemical synthesis), Antimalarials (chemistry), Antimalarials (pharmacology), Antimalarials (toxicity), Antiprotozoal agent, Antiviral, Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Antiviral Agents (toxicity), Biological activity, Chemical synthesis, Coronavirus, Drug Design, Ferrous Compounds (chemical synthesis), Ferrous Compounds (chemistry), Ferrous Compounds (pharmacology), Ferrous Compounds (toxicity), HIV-1 (drug effects), In vitro, Metallocene, Molecular Structure, Parasiticide, Plasmodium falciparum, Plasmodium falciparum (drug effects), Primary alcohol, Quinoline derivatives, Quinolines (chemical synthesis), Quinolines (chemistry), Quinolines (pharmacology), Quinolines (toxicity), SARS Virus (drug effects).
- MESH :
- chemical , chemical synthesis : Antimalarials, Antiviral Agents, Ferrous Compounds, Quinolines.
- chemical , chemistry : Antimalarials, Antiviral Agents, Ferrous Compounds, Quinolines.
- chemical , pharmacology : Antimalarials, Antiviral Agents, Ferrous Compounds, Quinolines.
- chemical , toxicity : Antimalarials, Antiviral Agents, Ferrous Compounds, Quinolines.
- drug effects : HIV-1, Plasmodium falciparum, SARS Virus.
- Animals, Drug Design, Molecular Structure.
Abstract
Three ferroquine (FQ) derivatives, closely mimicking the antimalarial drug hydroxychloroquine (HCQ), have been prepared. Whereas these organometallic compounds provide the expected reduced cytotoxic effects compared to FQ, they inhibit in vitro growth of Plasmodium falciparum far better than chloroquine (CQ). Moreover, this new class of bioorganometallic compounds exert antiviral effects with some selectivity toward SARS−CoV infection. These new drugs may offer an interesting alternative for Asia where SARS originated and malaria has remained endemic.
Url:
- https://api.istex.fr/ark:/67375/TPS-SBFQRQW9-N/fulltext.pdf
- https://hal.archives-ouvertes.fr/hal-00099876
DOI: 10.1021/jm0601856
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<title level="j" type="abbrev">J. Med. Chem.</title>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aminoalcohol</term>
<term>Animals</term>
<term>Antimalarial</term>
<term>Antimalarials (chemical synthesis)</term>
<term>Antimalarials (chemistry)</term>
<term>Antimalarials (pharmacology)</term>
<term>Antimalarials (toxicity)</term>
<term>Antiprotozoal agent</term>
<term>Antiviral</term>
<term>Antiviral Agents (chemical synthesis)</term>
<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Antiviral Agents (toxicity)</term>
<term>Biological activity</term>
<term>Chemical synthesis</term>
<term>Coronavirus</term>
<term>Drug Design</term>
<term>Ferrous Compounds (chemical synthesis)</term>
<term>Ferrous Compounds (chemistry)</term>
<term>Ferrous Compounds (pharmacology)</term>
<term>Ferrous Compounds (toxicity)</term>
<term>HIV-1 (drug effects)</term>
<term>In vitro</term>
<term>Metallocene</term>
<term>Molecular Structure</term>
<term>Parasiticide</term>
<term>Plasmodium falciparum</term>
<term>Plasmodium falciparum (drug effects)</term>
<term>Primary alcohol</term>
<term>Quinoline derivatives</term>
<term>Quinolines (chemical synthesis)</term>
<term>Quinolines (chemistry)</term>
<term>Quinolines (pharmacology)</term>
<term>Quinolines (toxicity)</term>
<term>SARS Virus (drug effects)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term>
<term>Antipaludiques ()</term>
<term>Antipaludiques (pharmacologie)</term>
<term>Antipaludiques (synthèse chimique)</term>
<term>Antipaludiques (toxicité)</term>
<term>Antiviraux ()</term>
<term>Antiviraux (pharmacologie)</term>
<term>Antiviraux (synthèse chimique)</term>
<term>Antiviraux (toxicité)</term>
<term>Composés du fer II ()</term>
<term>Composés du fer II (pharmacologie)</term>
<term>Composés du fer II (synthèse chimique)</term>
<term>Composés du fer II (toxicité)</term>
<term>Conception de médicament</term>
<term>Plasmodium falciparum ()</term>
<term>Quinoléines ()</term>
<term>Quinoléines (pharmacologie)</term>
<term>Quinoléines (synthèse chimique)</term>
<term>Quinoléines (toxicité)</term>
<term>Structure moléculaire</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term>
<term>Virus du SRAS ()</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antimalarials</term>
<term>Antiviral Agents</term>
<term>Ferrous Compounds</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antimalarials</term>
<term>Antiviral Agents</term>
<term>Ferrous Compounds</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antimalarials</term>
<term>Antiviral Agents</term>
<term>Ferrous Compounds</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="toxicity" xml:lang="en"><term>Antimalarials</term>
<term>Antiviral Agents</term>
<term>Ferrous Compounds</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term>
<term>Plasmodium falciparum</term>
<term>SARS Virus</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antipaludiques</term>
<term>Antiviraux</term>
<term>Composés du fer II</term>
<term>Quinoléines</term>
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<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antipaludiques</term>
<term>Antiviraux</term>
<term>Composés du fer II</term>
<term>Quinoléines</term>
</keywords>
<keywords scheme="MESH" qualifier="toxicité" xml:lang="fr"><term>Antipaludiques</term>
<term>Antiviraux</term>
<term>Composés du fer II</term>
<term>Quinoléines</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Animals</term>
<term>Drug Design</term>
<term>Molecular Structure</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Animaux</term>
<term>Antipaludiques</term>
<term>Antiviraux</term>
<term>Composés du fer II</term>
<term>Conception de médicament</term>
<term>Plasmodium falciparum</term>
<term>Quinoléines</term>
<term>Structure moléculaire</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term>
<term>Virus du SRAS</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Activité biologique</term>
<term>Alcool primaire</term>
<term>Aminoalcool</term>
<term>Antipaludique</term>
<term>Antiparasitaire</term>
<term>Antiprotozoaire</term>
<term>Antiviral</term>
<term>Coronavirus</term>
<term>Ethanolamine(N-[(2-[([7-chloro-4-quinolyl]amino)méthyl]ferrocényl)méthyl])</term>
<term>Ethanolamine(N-[(2-[([7-chloro-4-quinolyl]amino)méthyl]ferrocényl)méthyl]-N-méthyl)</term>
<term>Ethanolamine(N-[(2-[([7-chloro-4-quinolyl]amino)méthyl]ferrocényl)méthyl]-N-éthyl)</term>
<term>Ferrocène dérivé</term>
<term>In vitro</term>
<term>Métallocène</term>
<term>Plasmodium falciparum</term>
<term>Quinoléine dérivé</term>
<term>Synthèse chimique</term>
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<front><div type="abstract">Three ferroquine (FQ) derivatives, closely mimicking the antimalarial drug hydroxychloroquine (HCQ), have been prepared. Whereas these organometallic compounds provide the expected reduced cytotoxic effects compared to FQ, they inhibit in vitro growth of Plasmodium falciparum far better than chloroquine (CQ). Moreover, this new class of bioorganometallic compounds exert antiviral effects with some selectivity toward SARS−CoV infection. These new drugs may offer an interesting alternative for Asia where SARS originated and malaria has remained endemic.</div>
</front>
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<series><title level="j" type="main">Journal of medicinal chemistry : (Print)</title>
<title level="j" type="abbreviated">J. med. chem. : (Print)</title>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aminoalcohol</term>
<term>Antimalarial</term>
<term>Antiprotozoal agent</term>
<term>Antiviral</term>
<term>Biological activity</term>
<term>Chemical synthesis</term>
<term>Coronavirus</term>
<term>In vitro</term>
<term>Metallocene</term>
<term>Parasiticide</term>
<term>Plasmodium falciparum</term>
<term>Primary alcohol</term>
<term>Quinoline derivatives</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Synthèse chimique</term>
<term>Antipaludique</term>
<term>Antiviral</term>
<term>Activité biologique</term>
<term>Quinoléine dérivé</term>
<term>Aminoalcool</term>
<term>Alcool primaire</term>
<term>Plasmodium falciparum</term>
<term>Coronavirus</term>
<term>In vitro</term>
<term>Antiparasitaire</term>
<term>Antiprotozoaire</term>
<term>Métallocène</term>
<term>Ethanolamine(N-[(2-[([7-chloro-4-quinolyl]amino)méthyl]ferrocényl)méthyl])</term>
<term>Ethanolamine(N-[(2-[([7-chloro-4-quinolyl]amino)méthyl]ferrocényl)méthyl]-N-éthyl)</term>
<term>Ethanolamine(N-[(2-[([7-chloro-4-quinolyl]amino)méthyl]ferrocényl)méthyl]-N-méthyl)</term>
<term>Ferrocène dérivé</term>
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<front><div type="abstract" xml:lang="en">Three ferroquine (FQ) derivatives, closely mimicking the antimalarial drug hydroxychloroquine (HCQ), have been prepared. Whereas these organometallic compounds provide the expected reduced cytotoxic effects compared to FQ, they inhibit in vitro growth of Plasmodium falciparum far better than chloroquine (CQ). Moreover, this new class of bioorganometallic compounds exert antiviral effects with some selectivity toward SARS-CoV infection. These new drugs may offer an interesting alternative for Asia where SARS originated and malaria has remained endemic.</div>
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<author><name sortKey="Dive, Daniel" sort="Dive, Daniel" uniqKey="Dive D" first="Daniel" last="Dive">Daniel Dive</name>
<affiliation wicri:level="1"><country xml:lang="fr">Belgique</country>
<wicri:regionArea>Unité de Catalyse et Chimie du Solide - UMR CNRS 8181, ENSCL, Bâtiment C7, USTL, B.P. 90108, 59652, Villeneuve d' Ascq Cedex,France, Inserm, U547, Institut Pasteur, 1 rue du Pr Calmette, B.P. 245, 59019 Lille Cedex, France, UMR Université-INRA d’ImmunologieParasitaire, Faculté des Sciences Pharmaceutiques, 31, avenue Monge, Parc Grandmont, 37200 Tours, France, andRega Institute for Medical Research, K.U.Leuven, B-3000 Leuven</wicri:regionArea>
<wicri:noRegion>B-3000 Leuven</wicri:noRegion>
</affiliation>
<affiliation></affiliation>
</author>
<author><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="1"><country xml:lang="fr">Belgique</country>
<wicri:regionArea>Unité de Catalyse et Chimie du Solide - UMR CNRS 8181, ENSCL, Bâtiment C7, USTL, B.P. 90108, 59652, Villeneuve d' Ascq Cedex,France, Inserm, U547, Institut Pasteur, 1 rue du Pr Calmette, B.P. 245, 59019 Lille Cedex, France, UMR Université-INRA d’ImmunologieParasitaire, Faculté des Sciences Pharmaceutiques, 31, avenue Monge, Parc Grandmont, 37200 Tours, France, andRega Institute for Medical Research, K.U.Leuven, B-3000 Leuven</wicri:regionArea>
<wicri:noRegion>B-3000 Leuven</wicri:noRegion>
</affiliation>
<affiliation></affiliation>
</author>
</analytic>
<monogr></monogr>
<series><title level="j" type="main">Journal of Medicinal Chemistry</title>
<title level="j" type="abbrev">J. 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">2006</date>
<date type="published">2006</date>
<biblScope unit="vol">49</biblScope>
<biblScope unit="issue">9</biblScope>
<biblScope unit="page" from="2845">2845</biblScope>
<biblScope unit="page" to="2849">2849</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>Animals</term>
<term>Antimalarials (chemical synthesis)</term>
<term>Antimalarials (chemistry)</term>
<term>Antimalarials (pharmacology)</term>
<term>Antimalarials (toxicity)</term>
<term>Antiviral Agents (chemical synthesis)</term>
<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Antiviral Agents (toxicity)</term>
<term>Drug Design</term>
<term>Ferrous Compounds (chemical synthesis)</term>
<term>Ferrous Compounds (chemistry)</term>
<term>Ferrous Compounds (pharmacology)</term>
<term>Ferrous Compounds (toxicity)</term>
<term>HIV-1 (drug effects)</term>
<term>Molecular Structure</term>
<term>Plasmodium falciparum (drug effects)</term>
<term>Quinolines (chemical synthesis)</term>
<term>Quinolines (chemistry)</term>
<term>Quinolines (pharmacology)</term>
<term>Quinolines (toxicity)</term>
<term>SARS Virus (drug effects)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term>
<term>Antipaludiques ()</term>
<term>Antipaludiques (pharmacologie)</term>
<term>Antipaludiques (synthèse chimique)</term>
<term>Antipaludiques (toxicité)</term>
<term>Antiviraux ()</term>
<term>Antiviraux (pharmacologie)</term>
<term>Antiviraux (synthèse chimique)</term>
<term>Antiviraux (toxicité)</term>
<term>Composés du fer II ()</term>
<term>Composés du fer II (pharmacologie)</term>
<term>Composés du fer II (synthèse chimique)</term>
<term>Composés du fer II (toxicité)</term>
<term>Conception de médicament</term>
<term>Plasmodium falciparum ()</term>
<term>Quinoléines ()</term>
<term>Quinoléines (pharmacologie)</term>
<term>Quinoléines (synthèse chimique)</term>
<term>Quinoléines (toxicité)</term>
<term>Structure moléculaire</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term>
<term>Virus du SRAS ()</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antimalarials</term>
<term>Antiviral Agents</term>
<term>Ferrous Compounds</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antimalarials</term>
<term>Antiviral Agents</term>
<term>Ferrous Compounds</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antimalarials</term>
<term>Antiviral Agents</term>
<term>Ferrous Compounds</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="toxicity" xml:lang="en"><term>Antimalarials</term>
<term>Antiviral Agents</term>
<term>Ferrous Compounds</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term>
<term>Plasmodium falciparum</term>
<term>SARS Virus</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antipaludiques</term>
<term>Antiviraux</term>
<term>Composés du fer II</term>
<term>Quinoléines</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antipaludiques</term>
<term>Antiviraux</term>
<term>Composés du fer II</term>
<term>Quinoléines</term>
</keywords>
<keywords scheme="MESH" qualifier="toxicité" xml:lang="fr"><term>Antipaludiques</term>
<term>Antiviraux</term>
<term>Composés du fer II</term>
<term>Quinoléines</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Animals</term>
<term>Drug Design</term>
<term>Molecular Structure</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Animaux</term>
<term>Antipaludiques</term>
<term>Antiviraux</term>
<term>Composés du fer II</term>
<term>Conception de médicament</term>
<term>Plasmodium falciparum</term>
<term>Quinoléines</term>
<term>Structure moléculaire</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term>
<term>Virus du SRAS</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract">Three ferroquine (FQ) derivatives, closely mimicking the antimalarial drug hydroxychloroquine (HCQ), have been prepared. Whereas these organometallic compounds provide the expected reduced cytotoxic effects compared to FQ, they inhibit in vitro growth of Plasmodium falciparum far better than chloroquine (CQ). Moreover, this new class of bioorganometallic compounds exert antiviral effects with some selectivity toward SARS−CoV infection. These new drugs may offer an interesting alternative for Asia where SARS originated and malaria has remained endemic.</div>
</front>
</TEI>
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