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New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities

Identifieur interne : 000099 ( France/Analysis ); précédent : 000098; suivant : 000100

New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities

Auteurs : Aida Chaker [France] ; Ennaji Najahi [France] ; Olivier Chatriant [France] ; Alexis Valentin [France] ; Nathan Téné [France] ; Michel Treilhou [France] ; Fakher Chabchoub [Tunisie] ; Françoise Nepveu [France]

Source :

RBID : Hal:hal-02417861

English descriptors

Abstract

A new series of 3-substituted-2,1-benzisoxazoles (anthranils) were prepared by different methods and characterized by spectroscopic methods and mass spectrometry. These 2,1-benzisox-azoles were tested in vitro for their antiplasmodial activity on a chloroquine-resistant strain of Plasmodium falciparum (P.f.) (FcB1), and for antimicrobial activity against representative bacterial and fungal strains, as well as for cytotoxicity on MCF7 human breast cancer cells. Given the log P calc and selectivity index values (cytotoxicity/antiplasmodial activity ratio), the benzo[c]isoxazol-3-ylmethylene-phenyl-amine (11) (imino-benzisoxazole) was identified as the best hit against P.f. (FcB1), and the benzo[c]isoxazol-3-yl-phenyl-methanone (3) (3-acyl-2,1-benzisoxazole) against P.f. and the Geotrichum candidum fungal strain.


Url:
DOI: 10.1016/j.arabjc.2013.09.011


Affiliations:


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Hal:hal-02417861

Le document en format XML

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<idno type="DOI">10.1016/j.arabjc.2013.09.011</idno>
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<title level="j">Arabian Journal of Chemistry</title>
<idno type="ISSN">1878-5352</idno>
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<date type="datePub">2017-05</date>
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<term>1-Benzisoxazole</term>
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<p>A new series of 3-substituted-2,1-benzisoxazoles (anthranils) were prepared by different methods and characterized by spectroscopic methods and mass spectrometry. These 2,1-benzisox-azoles were tested in vitro for their antiplasmodial activity on a chloroquine-resistant strain of Plasmodium falciparum (P.f.) (FcB1), and for antimicrobial activity against representative bacterial and fungal strains, as well as for cytotoxicity on MCF7 human breast cancer cells. Given the log P calc and selectivity index values (cytotoxicity/antiplasmodial activity ratio), the benzo[c]isoxazol-3-ylmethylene-phenyl-amine (11) (imino-benzisoxazole) was identified as the best hit against P.f. (FcB1), and the benzo[c]isoxazol-3-yl-phenyl-methanone (3) (3-acyl-2,1-benzisoxazole) against P.f. and the Geotrichum candidum fungal strain.</p>
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<name sortKey="Chatriant, Olivier" sort="Chatriant, Olivier" uniqKey="Chatriant O" first="Olivier" last="Chatriant">Olivier Chatriant</name>
<name sortKey="Najahi, Ennaji" sort="Najahi, Ennaji" uniqKey="Najahi E" first="Ennaji" last="Najahi">Ennaji Najahi</name>
<name sortKey="Nepveu, Francoise" sort="Nepveu, Francoise" uniqKey="Nepveu F" first="Françoise" last="Nepveu">Françoise Nepveu</name>
<name sortKey="Tene, Nathan" sort="Tene, Nathan" uniqKey="Tene N" first="Nathan" last="Téné">Nathan Téné</name>
<name sortKey="Treilhou, Michel" sort="Treilhou, Michel" uniqKey="Treilhou M" first="Michel" last="Treilhou">Michel Treilhou</name>
<name sortKey="Valentin, Alexis" sort="Valentin, Alexis" uniqKey="Valentin A" first="Alexis" last="Valentin">Alexis Valentin</name>
</country>
<country name="Tunisie">
<noRegion>
<name sortKey="Chabchoub, Fakher" sort="Chabchoub, Fakher" uniqKey="Chabchoub F" first="Fakher" last="Chabchoub">Fakher Chabchoub</name>
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</country>
</tree>
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</record>

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