Looking for new antiplasmodial quinazolines: DMAP-catalyzed synthesis of 4-benzyloxy- and 4-aryloxy-2-trichloromethylquinazolines and their in vitro evaluation toward Plasmodium falciparum
Identifieur interne : 000109 ( France/Analysis ); précédent : 000108; suivant : 000110Looking for new antiplasmodial quinazolines: DMAP-catalyzed synthesis of 4-benzyloxy- and 4-aryloxy-2-trichloromethylquinazolines and their in vitro evaluation toward Plasmodium falciparum
Auteurs : Armand Gellis [France] ; Nicolas Primas [France] ; Sébastien Hutter [France] ; Gilles Lanzada [France] ; Vincent Remusat [France] ; Pierre Verhaeghe [France] ; Patrice Vanelle [France] ; Nadine Azas [France]Source :
- European Journal of Medicinal Chemistry [ 0223-5234 ] ; 2016.
English descriptors
- mix :
Abstract
A DMAP catalyzedsynthesis of new 4-benzyloxy-and 4-aryloxy-2-trichloromethylquinazolines was studied, in a view to react 4-chloroquinazolines with poorly nucleophilic alcohols such as benzylic alcohols, via a simple and cheapS N Ar reaction approach. A fast (1 h) general operating procedure, affording good reaction yields,was achieved under microwave irradiation. Thus, a series of 35 molecules was obtained and evaluated in vitro on the K1 multi-resistant P. falciparum strain, in parallel with a cytotoxicity assessment on the human HepG2 cell line. 5 hit-molecules were identified, presenting both promising antiplasmodial activity (1.5 µM < IC 50 < 2 µM) and low cytotoxicities (25 µM < CC 50 < 45 µM). Apart for 2 molecules, the global series displayed a satisfying solubility in the aqueous biological media. Structure-activity relationships showed that the molecules presenting a benzyloxy moiety were less cytotoxic than the ones bearing a phenoxy moiety at position 4 of the quinazoline ring. It also appeared that the introduction of a heteroaryl moiety afforded inactive compounds. Finally, the most active and selective molecules (Selectivity index = 22-27) were the ones presenting either an unsubstituted benzyloxy group or a phenoxy group, this last bearing a p-bromo or an o-acetyl substituent. Highlights:► The DMAP-catalyzed S N Ar reactionbetween 4-chloro-2-trichloromethylquinazoline and various alcohols or phenols was studied. ► A series of 35 new quinazolineswas synthesized in good yields. ►In vitroevaluationwas made on Plasmodium falciparum.► 5 selective antiplasmodial hit molecules were identified.
Url:
DOI: 10.1016/j.ejmech.2016.04.059
Affiliations:
Links toward previous steps (curation, corpus...)
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Hal:hal-01417007Le document en format XML
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<ref type="url">http://icr-amu.cnrs.fr/</ref>
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<idno type="ISNI">0000 0001 2176 4817</idno>
<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>
</address>
<ref type="url">http://www.univ-amu.fr/</ref>
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<idno type="ISNI">0000000122597504</idno>
<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>
<ref type="url">http://www.cnrs.fr/</ref>
</desc>
</org>
</tutelle>
</tutelles>
</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>
<author><name sortKey="Azas, Nadine" sort="Azas, Nadine" uniqKey="Azas N" first="Nadine" last="Azas">Nadine Azas</name>
<affiliation wicri:level="1"><hal:affiliation type="laboratory" xml:id="struct-220808" status="OLD"> <idno type="RNSR">200817410U</idno>
<orgName>Infections Parasitaires : Transmission, Physiopathologie et Thérapeutiques</orgName>
<orgName type="acronym">IP-TPT</orgName>
<date type="start">2008-01-01</date>
<date type="end">2017-12-31</date>
<desc> <address> <addrLine>Faculté de Pharmacie27 bd Jean Moulin CS 3006413385 Marseille </addrLine>
<country key="FR"></country>
</address>
<ref type="url">http://pharmacie.univ-amu.fr/umr-md3</ref>
</desc>
<listRelation> <relation name="UMR MD3" active="#struct-300092" type="direct"></relation>
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<desc> <address> <country key="FR"></country>
</address>
</desc>
</org>
</tutelle>
<tutelle name="UMR MD3" active="#struct-300073" type="direct"><org type="institution" xml:id="struct-300073" status="VALID"> <orgName>Assistance Publique - Hôpitaux de Marseille</orgName>
<orgName type="acronym">APHM</orgName>
<desc> <address> <addrLine>Direction générale AP-HM80, rue Brochier13 354 Marseille Cedex 5</addrLine>
<country key="FR"></country>
</address>
<ref type="url">http://fr.ap-hm.fr/</ref>
</desc>
</org>
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<idno type="ISNI">0000 0001 2176 4817</idno>
<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>
</address>
<ref type="url">http://www.univ-amu.fr/</ref>
</desc>
</org>
</tutelle>
<tutelle name="UMR MD3" active="#struct-67872" type="direct"><org type="institution" xml:id="struct-67872" status="VALID"> <orgName>Institut de Recherche pour le Développement</orgName>
<orgName type="acronym">IRD</orgName>
<desc> <address> <addrLine>SiègeLe Sextant 44, bd de DunkerqueCS 9000913572 Marseille cedex 02</addrLine>
<country key="FR"></country>
</address>
<ref type="url">http://www.ird.fr/</ref>
</desc>
</org>
</tutelle>
</tutelles>
</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.2016.04.059</idno>
<series><title level="j">European Journal of Medicinal Chemistry</title>
<idno type="ISSN">0223-5234</idno>
<imprint><date type="datePub">2016</date>
</imprint>
</series>
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</fileDesc>
<profileDesc><textClass><keywords scheme="mix" xml:lang="en"><term> SARs</term>
<term> SNAr reaction</term>
<term> microwave-assisted chemistry</term>
<term>2-trichloromethylquinazoline</term>
<term>4-benzyloxyquinazoline</term>
<term>4-phenoxyquinazoline</term>
<term>DMAP-catalysis</term>
<term>HepG2 cytotoxicity</term>
<term>Plasmodium falciparum</term>
<term>antiplasmodial activity</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en"> <p>A DMAP catalyzedsynthesis of new 4-benzyloxy-and 4-aryloxy-2-trichloromethylquinazolines was studied, in a view to react 4-chloroquinazolines with poorly nucleophilic alcohols such as benzylic alcohols, via a simple and cheapS N Ar reaction approach. A fast (1 h) general operating procedure, affording good reaction yields,was achieved under microwave irradiation. Thus, a series of 35 molecules was obtained and evaluated in vitro on the K1 multi-resistant P. falciparum strain, in parallel with a cytotoxicity assessment on the human HepG2 cell line. 5 hit-molecules were identified, presenting both promising antiplasmodial activity (1.5 µM < IC 50 < 2 µM) and low cytotoxicities (25 µM < CC 50 < 45 µM). Apart for 2 molecules, the global series displayed a satisfying solubility in the aqueous biological media. Structure-activity relationships showed that the molecules presenting a benzyloxy moiety were less cytotoxic than the ones bearing a phenoxy moiety at position 4 of the quinazoline ring. It also appeared that the introduction of a heteroaryl moiety afforded inactive compounds. Finally, the most active and selective molecules (Selectivity index = 22-27) were the ones presenting either an unsubstituted benzyloxy group or a phenoxy group, this last bearing a p-bromo or an o-acetyl substituent. Highlights:► The DMAP-catalyzed S N Ar reactionbetween 4-chloro-2-trichloromethylquinazoline and various alcohols or phenols was studied. ► A series of 35 new quinazolineswas synthesized in good yields. ►In vitroevaluationwas made on Plasmodium falciparum.► 5 selective antiplasmodial hit molecules were identified.</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="Gellis, Armand" sort="Gellis, Armand" uniqKey="Gellis A" first="Armand" last="Gellis">Armand Gellis</name>
</region>
<name sortKey="Azas, Nadine" sort="Azas, Nadine" uniqKey="Azas N" first="Nadine" last="Azas">Nadine Azas</name>
<name sortKey="Hutter, Sebastien" sort="Hutter, Sebastien" uniqKey="Hutter S" first="Sébastien" last="Hutter">Sébastien Hutter</name>
<name sortKey="Lanzada, Gilles" sort="Lanzada, Gilles" uniqKey="Lanzada G" first="Gilles" last="Lanzada">Gilles Lanzada</name>
<name sortKey="Primas, Nicolas" sort="Primas, Nicolas" uniqKey="Primas N" first="Nicolas" last="Primas">Nicolas Primas</name>
<name sortKey="Remusat, Vincent" sort="Remusat, Vincent" uniqKey="Remusat V" first="Vincent" last="Remusat">Vincent Remusat</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>
</tree>
</affiliations>
</record>
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