Synthesis and Antimalarial Activity in Vitro and in Vivo of a New Ferrocene−Chloroquine Analogue
The antimalarial activities of ferrocenic compounds mimicking chloroquine and active upon chloroquine-resistant strains of Plasmodium falciparum were evaluated. Four 7-chloro-4-[[[2-[(N,N-substituted amino)methyl]ferrocenyl]methyl]amino]quinoline derivatives have been synthesized; one of them, 1a, s...
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Veröffentlicht in: | Journal of medicinal chemistry 1997-11, Vol.40 (23), p.3715-3718 |
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container_title | Journal of medicinal chemistry |
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creator | Biot, Christophe Glorian, Guillaume Maciejewski, Lucien A Brocard, Jacques S Domarle, Olivier Blampain, Georgette Millet, Pascal Georges, Alain J Abessolo, Huguette Dive, Daniel Lebibi, Jacques |
description | The antimalarial activities of ferrocenic compounds mimicking chloroquine and active upon chloroquine-resistant strains of Plasmodium falciparum were evaluated. Four 7-chloro-4-[[[2-[(N,N-substituted amino)methyl]ferrocenyl]methyl]amino]quinoline derivatives have been synthesized; one of them, 1a, showed high potent antimalarial activity in vivo on mice infected with Plasmodium berghei N. and Plasmodium yoelii NS. and was 22 times more potent against schizontocides than chloroquine in vitro against a drug-resistant strain of P. falciparum. |
doi_str_mv | 10.1021/jm970401y |
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Four 7-chloro-4-[[[2-[(N,N-substituted amino)methyl]ferrocenyl]methyl]amino]quinoline derivatives have been synthesized; one of them, 1a, showed high potent antimalarial activity in vivo on mice infected with Plasmodium berghei N. and Plasmodium yoelii NS. and was 22 times more potent against schizontocides than chloroquine in vitro against a drug-resistant strain of P. falciparum.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm970401y</identifier><identifier>PMID: 9371235</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antimalarials - chemical synthesis ; Antimalarials - pharmacology ; Antiparasitic agents ; Biological and medical sciences ; Chloroquine - analogs & derivatives ; Chloroquine - chemical synthesis ; Chloroquine - pharmacology ; Female ; Ferrous Compounds - chemical synthesis ; Ferrous Compounds - pharmacology ; Malaria - blood ; Malaria - drug therapy ; Medical sciences ; Metallocenes ; Mice ; Pharmacology. Drug treatments ; Plasmodium berghei - drug effects ; Plasmodium falciparum - drug effects ; Plasmodium yoelii - drug effects</subject><ispartof>Journal of medicinal chemistry, 1997-11, Vol.40 (23), p.3715-3718</ispartof><rights>Copyright © 1997 American Chemical Society</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a377t-f010960c53b8c8f9170ddbe8bc5bc5aad777216c51c5eeaabba1f615a36e1e983</citedby><cites>FETCH-LOGICAL-a377t-f010960c53b8c8f9170ddbe8bc5bc5aad777216c51c5eeaabba1f615a36e1e983</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm970401y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm970401y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2066327$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9371235$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Biot, Christophe</creatorcontrib><creatorcontrib>Glorian, Guillaume</creatorcontrib><creatorcontrib>Maciejewski, Lucien A</creatorcontrib><creatorcontrib>Brocard, Jacques S</creatorcontrib><creatorcontrib>Domarle, Olivier</creatorcontrib><creatorcontrib>Blampain, Georgette</creatorcontrib><creatorcontrib>Millet, Pascal</creatorcontrib><creatorcontrib>Georges, Alain J</creatorcontrib><creatorcontrib>Abessolo, Huguette</creatorcontrib><creatorcontrib>Dive, Daniel</creatorcontrib><creatorcontrib>Lebibi, Jacques</creatorcontrib><title>Synthesis and Antimalarial Activity in Vitro and in Vivo of a New Ferrocene−Chloroquine Analogue</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The antimalarial activities of ferrocenic compounds mimicking chloroquine and active upon chloroquine-resistant strains of Plasmodium falciparum were evaluated. Four 7-chloro-4-[[[2-[(N,N-substituted amino)methyl]ferrocenyl]methyl]amino]quinoline derivatives have been synthesized; one of them, 1a, showed high potent antimalarial activity in vivo on mice infected with Plasmodium berghei N. and Plasmodium yoelii NS. and was 22 times more potent against schizontocides than chloroquine in vitro against a drug-resistant strain of P. falciparum.</description><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antimalarials - chemical synthesis</subject><subject>Antimalarials - pharmacology</subject><subject>Antiparasitic agents</subject><subject>Biological and medical sciences</subject><subject>Chloroquine - analogs & derivatives</subject><subject>Chloroquine - chemical synthesis</subject><subject>Chloroquine - pharmacology</subject><subject>Female</subject><subject>Ferrous Compounds - chemical synthesis</subject><subject>Ferrous Compounds - pharmacology</subject><subject>Malaria - blood</subject><subject>Malaria - drug therapy</subject><subject>Medical sciences</subject><subject>Metallocenes</subject><subject>Mice</subject><subject>Pharmacology. Drug treatments</subject><subject>Plasmodium berghei - drug effects</subject><subject>Plasmodium falciparum - drug effects</subject><subject>Plasmodium yoelii - drug effects</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMFu1DAQhi0EKkvhwAMg-QBIHAJje2Mnx9WKUqCCopZerYkzoV6ycbGTwr4BZx6RJ8HbXe0JaSSP9X_69c_P2FMBrwVI8Wa1rg3MQWzusZkoJRTzCub32QxAykJqqR6yRymtAEAJqY7YUa1MXsoZay42w3hNySeOQ8sXw-jX2GP02POFG_2tHzfcD_zKjzHcIXef28BDx5F_op_8hGIMjgb6-_vP8roPMfyY_EDZC_vwbaLH7EGHfaIn-_eYfT15e7k8Lc4-v3u_XJwVqIwZiw4E1BpcqZrKVV0tDLRtQ1XjyjyIrTFGCu1K4UoixKZB0WlRotIkqK7UMXu5873ZJqA02rVPjvoeBwpTsqaeC6mVyOCrHehiSClSZ29ivjpurAC77dMe-szss73p1KypPZD7ArP-fK9jcth3EQfn0wGToLWSJmPFDvNppF8HGeN3q40ypb08v7DnH68UfDn9YLcRX-x4dMmuwhRzl-k_8f4BGSKZwA</recordid><startdate>19971107</startdate><enddate>19971107</enddate><creator>Biot, Christophe</creator><creator>Glorian, Guillaume</creator><creator>Maciejewski, Lucien A</creator><creator>Brocard, Jacques S</creator><creator>Domarle, Olivier</creator><creator>Blampain, Georgette</creator><creator>Millet, Pascal</creator><creator>Georges, Alain J</creator><creator>Abessolo, Huguette</creator><creator>Dive, Daniel</creator><creator>Lebibi, Jacques</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19971107</creationdate><title>Synthesis and Antimalarial Activity in Vitro and in Vivo of a New Ferrocene−Chloroquine Analogue</title><author>Biot, Christophe ; Glorian, Guillaume ; Maciejewski, Lucien A ; Brocard, Jacques S ; Domarle, Olivier ; Blampain, Georgette ; Millet, Pascal ; Georges, Alain J ; Abessolo, Huguette ; Dive, Daniel ; Lebibi, Jacques</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a377t-f010960c53b8c8f9170ddbe8bc5bc5aad777216c51c5eeaabba1f615a36e1e983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>Animals</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antimalarials - chemical synthesis</topic><topic>Antimalarials - pharmacology</topic><topic>Antiparasitic agents</topic><topic>Biological and medical sciences</topic><topic>Chloroquine - analogs & derivatives</topic><topic>Chloroquine - chemical synthesis</topic><topic>Chloroquine - pharmacology</topic><topic>Female</topic><topic>Ferrous Compounds - chemical synthesis</topic><topic>Ferrous Compounds - pharmacology</topic><topic>Malaria - blood</topic><topic>Malaria - drug therapy</topic><topic>Medical sciences</topic><topic>Metallocenes</topic><topic>Mice</topic><topic>Pharmacology. Drug treatments</topic><topic>Plasmodium berghei - drug effects</topic><topic>Plasmodium falciparum - drug effects</topic><topic>Plasmodium yoelii - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Biot, Christophe</creatorcontrib><creatorcontrib>Glorian, Guillaume</creatorcontrib><creatorcontrib>Maciejewski, Lucien A</creatorcontrib><creatorcontrib>Brocard, Jacques S</creatorcontrib><creatorcontrib>Domarle, Olivier</creatorcontrib><creatorcontrib>Blampain, Georgette</creatorcontrib><creatorcontrib>Millet, Pascal</creatorcontrib><creatorcontrib>Georges, Alain J</creatorcontrib><creatorcontrib>Abessolo, Huguette</creatorcontrib><creatorcontrib>Dive, Daniel</creatorcontrib><creatorcontrib>Lebibi, Jacques</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Biot, Christophe</au><au>Glorian, Guillaume</au><au>Maciejewski, Lucien A</au><au>Brocard, Jacques S</au><au>Domarle, Olivier</au><au>Blampain, Georgette</au><au>Millet, Pascal</au><au>Georges, Alain J</au><au>Abessolo, Huguette</au><au>Dive, Daniel</au><au>Lebibi, Jacques</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Antimalarial Activity in Vitro and in Vivo of a New Ferrocene−Chloroquine Analogue</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1997-11-07</date><risdate>1997</risdate><volume>40</volume><issue>23</issue><spage>3715</spage><epage>3718</epage><pages>3715-3718</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The antimalarial activities of ferrocenic compounds mimicking chloroquine and active upon chloroquine-resistant strains of Plasmodium falciparum were evaluated. Four 7-chloro-4-[[[2-[(N,N-substituted amino)methyl]ferrocenyl]methyl]amino]quinoline derivatives have been synthesized; one of them, 1a, showed high potent antimalarial activity in vivo on mice infected with Plasmodium berghei N. and Plasmodium yoelii NS. and was 22 times more potent against schizontocides than chloroquine in vitro against a drug-resistant strain of P. falciparum.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>9371235</pmid><doi>10.1021/jm970401y</doi><tpages>4</tpages></addata></record> |
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subjects | Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antimalarials - chemical synthesis Antimalarials - pharmacology Antiparasitic agents Biological and medical sciences Chloroquine - analogs & derivatives Chloroquine - chemical synthesis Chloroquine - pharmacology Female Ferrous Compounds - chemical synthesis Ferrous Compounds - pharmacology Malaria - blood Malaria - drug therapy Medical sciences Metallocenes Mice Pharmacology. Drug treatments Plasmodium berghei - drug effects Plasmodium falciparum - drug effects Plasmodium yoelii - drug effects |
title | Synthesis and Antimalarial Activity in Vitro and in Vivo of a New Ferrocene−Chloroquine Analogue |
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