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Discovery of new thienopyrimidinone derivatives displaying antimalarial properties toward both erythrocytic and hepatic stages of Plasmodium

Identifieur interne : 000137 ( France/Analysis ); précédent : 000136; suivant : 000138

Discovery of new thienopyrimidinone derivatives displaying antimalarial properties toward both erythrocytic and hepatic stages of Plasmodium

Auteurs : Anita Cohen [France] ; Peggy Suzanne [France] ; Jean-Charles Lancelot [France] ; Pierre Verhaeghe [France] ; Aurélien Lesnard [France] ; Louise Basmaciyan [France] ; Sébastien Hutter [France] ; Michèle Laget [France] ; Aurélien Dumètre [France] ; Lucie Paloque [France] ; Eric Deharo [France] ; Maxime D. Crozet [France] ; Pascal Rathelot [France] ; Patrick Dallemagne [France] ; Audrey Lorthiois [France] ; Carol Hopkins Sibley [États-Unis] ; Patrice Vanelle [France] ; Alexis Valentin [France] ; Dominique Mazier [France] ; Sylvain Rault [France] ; Nadine Azas [France]

Source :

RBID : Hal:hal-01460555

Abstract

A preliminary in vitro screening of compounds belonging to various chemical families from our library revealed the thieno[3,2-d]pyrimidin-4(3H)-one scaffold displayed a promising profile against Plasmodium falciparum. Then, 120 new derivatives were synthesized and evaluated in vitro; compared to drug references, 40 showed good activity toward chloroquine sensitive (IC50 35-344 nM) and resistant (IC50 45-800 nM) P. falciparum strains. They were neither cytotoxic (CC50 15-50 mu M) toward HepG2 and CHO cells, nor mutagenic. Structure activity relationships were defined. The lead-compound also appeared active against the Plasmodium liver stages (Plasmodium yoelii IC50 = 35 nM) and a preliminary in vivo evaluation indicated the in vitro activity was preserved (45% reduction in parasitemia compared to untreated infected mice). A mechanistic study demonstrated these molecules do not involve any of the pathways described for commercial drugs and exert a specific activity on the ring and trophozoite stages. 2015 Elsevier Masson SAS. All rights reserved.


Url:
DOI: 10.1016/j.ejmech.2015.03.011


Affiliations:

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Hal:hal-01460555

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<idno type="DOI">10.1016/j.ejmech.2015.03.011</idno>
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<title level="j">European Journal of Medicinal Chemistry</title>
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<date type="datePub">2015-05</date>
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<p>A preliminary in vitro screening of compounds belonging to various chemical families from our library revealed the thieno[3,2-d]pyrimidin-4(3H)-one scaffold displayed a promising profile against Plasmodium falciparum. Then, 120 new derivatives were synthesized and evaluated in vitro; compared to drug references, 40 showed good activity toward chloroquine sensitive (IC50 35-344 nM) and resistant (IC50 45-800 nM) P. falciparum strains. They were neither cytotoxic (CC50 15-50 mu M) toward HepG2 and CHO cells, nor mutagenic. Structure activity relationships were defined. The lead-compound also appeared active against the Plasmodium liver stages (Plasmodium yoelii IC50 = 35 nM) and a preliminary in vivo evaluation indicated the in vitro activity was preserved (45% reduction in parasitemia compared to untreated infected mice). A mechanistic study demonstrated these molecules do not involve any of the pathways described for commercial drugs and exert a specific activity on the ring and trophozoite stages. 2015 Elsevier Masson SAS. All rights reserved.</p>
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