ChloroquineV1, France, Analysis, bibRecord, 000251

Original quinazoline derivatives displaying antiplasmodial properties

Identifieur interne : 000251 ( France/Analysis ); précédent : 000250; suivant : 000252

Original quinazoline derivatives displaying antiplasmodial properties

Auteurs : Youssef Kabri [France] ; Nadine Azas [France] ; Aurélien Dumètre [France] ; Sébastien Hutter [France] ; Michèle Laget [France] ; Pierre Verhaeghe [France] ; Armand Gellis [France] ; Patrice Vanelle [France]

Source :

European Journal of Medicinal Chemistry [ 0223-5234 ] ; 2010-02.

RBID : Hal:hal-01460232

Abstract

The multistep synthesis of new quinazoline-derived molecules and their in vitro antiplasmodial evaluation on the W2 chloroquino-resistant Plasmodium falciparum strain is described herein. These molecules have also been studied concerning their in vitro cytotoxicity toward two human cell lines (K652 and HepG2) in order to calculate their respective selectivity indexes (S.I.). Among the fourteen tested molecules, two exhibited both significant antiplasmodial activity (IC(50) = 0.95 and 1.3 mu M) and low toxicity (IC(50) \textgreater 100 or 125 mu M), compared with two reference drugs: chloroquine and doxycycline. The structure activity relationships establish that the molecular scaffold which exerts the best profile is the 6-nitro-2-(tosylmethyl)-N-(3-substituted-phenyl)-quinazolin-4-amine. The hit molecules were finally investigated regarding their potential action toward two other protozoa, Leishmania donovani and Toxoplasma gondii, showing that these molecules display a selective antiplasmodial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.

Url:

https://hal.archives-ouvertes.fr/hal-01460232

DOI: 10.1016/j.ejmech.2009.11.005

Affiliations:

Links toward previous steps (curation, corpus...)

to stream Hal, to step Corpus: 000177
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to stream Main, to step Exploration: 001609
to stream France, to step Extraction: 000251

Links to Exploration step

Hal:hal-01460232

Le document en format XML

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<placeName><settlement type="city">Marseille</settlement>
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<orgName type="university">Université d'Aix-Marseille</orgName>
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<author><name sortKey="Verhaeghe, Pierre" sort="Verhaeghe, Pierre" uniqKey="Verhaeghe P" first="Pierre" last="Verhaeghe">Pierre Verhaeghe</name>
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              <country key="FR"></country>
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          <orgName type="acronym">ICT-FR 2599</orgName>
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<country>France</country>
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</author>
<author><name sortKey="Gellis, Armand" sort="Gellis, Armand" uniqKey="Gellis A" first="Armand" last="Gellis">Armand Gellis</name>
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          <orgName>Institut de Chimie Radicalaire</orgName>
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<country>France</country>
<placeName><settlement type="city">Marseille</settlement>
<region type="region" nuts="2">Provence-Alpes-Côte d'Azur</region>
</placeName>
<orgName type="university">Université d'Aix-Marseille</orgName>
</affiliation>
</author>
<author><name sortKey="Vanelle, Patrice" sort="Vanelle, Patrice" uniqKey="Vanelle P" first="Patrice" last="Vanelle">Patrice Vanelle</name>
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          <orgName>Institut de Chimie Radicalaire</orgName>
          <orgName type="acronym">ICR</orgName>
          <date type="start">2012</date>
          <desc>            <address>              <addrLine>Avenue Escadrille Normandie-Niemen Service D42 13397 Marseille cedex 20</addrLine>
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          <orgName>Aix Marseille Université</orgName>
          <orgName type="acronym">AMU</orgName>
          <date type="start">2012-01-01</date>
          <desc>            <address>              <addrLine>Aix-Marseille UniversitéJardins du Pharo58 Boulevard Charles Livon13284 Marseille cedex 7</addrLine>
              <country key="FR"></country>
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          <orgName>Centre National de la Recherche Scientifique</orgName>
          <orgName type="acronym">CNRS</orgName>
          <date type="start">1939-10-19</date>
          <desc>            <address>              <country key="FR"></country>
            </address>
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          </desc>
        </org>
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</hal:affiliation>
<country>France</country>
<placeName><settlement type="city">Marseille</settlement>
<region type="region" nuts="2">Provence-Alpes-Côte d'Azur</region>
</placeName>
<orgName type="university">Université d'Aix-Marseille</orgName>
</affiliation>
</author>
</analytic>
<idno type="DOI">10.1016/j.ejmech.2009.11.005</idno>
<series><title level="j">European Journal of Medicinal Chemistry</title>
<idno type="ISSN">0223-5234</idno>
<imprint><date type="datePub">2010-02</date>
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<front><div type="abstract" xml:lang="en">              <p>The multistep synthesis of new quinazoline-derived molecules and their in vitro antiplasmodial evaluation on the W2 chloroquino-resistant Plasmodium falciparum strain is described herein. These molecules have also been studied concerning their in vitro cytotoxicity toward two human cell lines (K652 and HepG2) in order to calculate their respective selectivity indexes (S.I.). Among the fourteen tested molecules, two exhibited both significant antiplasmodial activity (IC(50) = 0.95 and 1.3 mu M) and low toxicity (IC(50) \textgreater 100 or 125 mu M), compared with two reference drugs: chloroquine and doxycycline. The structure activity relationships establish that the molecular scaffold which exerts the best profile is the 6-nitro-2-(tosylmethyl)-N-(3-substituted-phenyl)-quinazolin-4-amine. The hit molecules were finally investigated regarding their potential action toward two other protozoa, Leishmania donovani and Toxoplasma gondii, showing that these molecules display a selective antiplasmodial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.</p>
            </div>
</front>
</TEI>
<affiliations><list><country><li>France</li>
</country>
<region><li>Provence-Alpes-Côte d'Azur</li>
</region>
<settlement><li>Marseille</li>
</settlement>
<orgName><li>Université d'Aix-Marseille</li>
</orgName>
</list>
<tree><country name="France"><region name="Provence-Alpes-Côte d'Azur"><name sortKey="Kabri, Youssef" sort="Kabri, Youssef" uniqKey="Kabri Y" first="Youssef" last="Kabri">Youssef Kabri</name>
</region>
<name sortKey="Azas, Nadine" sort="Azas, Nadine" uniqKey="Azas N" first="Nadine" last="Azas">Nadine Azas</name>
<name sortKey="Dumetre, Aurelien" sort="Dumetre, Aurelien" uniqKey="Dumetre A" first="Aurélien" last="Dumètre">Aurélien Dumètre</name>
<name sortKey="Gellis, Armand" sort="Gellis, Armand" uniqKey="Gellis A" first="Armand" last="Gellis">Armand Gellis</name>
<name sortKey="Hutter, Sebastien" sort="Hutter, Sebastien" uniqKey="Hutter S" first="Sébastien" last="Hutter">Sébastien Hutter</name>
<name sortKey="Laget, Michele" sort="Laget, Michele" uniqKey="Laget M" first="Michèle" last="Laget">Michèle Laget</name>
<name sortKey="Vanelle, Patrice" sort="Vanelle, Patrice" uniqKey="Vanelle P" first="Patrice" last="Vanelle">Patrice Vanelle</name>
<name sortKey="Verhaeghe, Pierre" sort="Verhaeghe, Pierre" uniqKey="Verhaeghe P" first="Pierre" last="Verhaeghe">Pierre Verhaeghe</name>
</country>
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</record>

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Original quinazoline derivatives displaying antiplasmodial properties

Original quinazoline derivatives displaying antiplasmodial properties

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