Marin A., Lima L. M., Solano B., Vicente E., Silanes S. P., Maurel Séverine, Sauvain Michel, Aldana I., Monge A., Deharo Eric. (2008). Antiplasmodial structure-activity relationship of 3-trifluoromethyl-2-arylcarbonylquinoxaline 1,4-di-N-oxide derivatives. Experimental Parasitology, 118 (1), p. 25-31. ISSN 0014-4894.
Titre du document
Antiplasmodial structure-activity relationship of 3-trifluoromethyl-2-arylcarbonylquinoxaline 1,4-di-N-oxide derivatives
Marin A., Lima L. M., Solano B., Vicente E., Silanes S. P., Maurel Séverine, Sauvain Michel, Aldana I., Monge A., Deharo Eric
Source
Experimental Parasitology, 2008,
118 (1), p. 25-31 ISSN 0014-4894
Derivatives of 3-trifluoromethyl-2-arylcarbonylquinoxaline 1,4-di-N-oxide (4b-g, 5b-g, 6a-g) were synthesized and evaluated for their capacity to inhibit the growth of chloroquine-resistant Plasmodium falciparum FCB1 strain in culture. Compound 7-chloro-2-(2-furylcarbonyl)-3-trifluoromethyl-1,4-quinoxaline di-N-oxide (5g) was the most active being almost 5 times more active than chloroquine. It was also 50 times more active against P. falciparum than toxic toward MCF7 cells. Structural characteristics for a quinoxaline to be active were defined: bioisosteric modification of phenyl group by 2-thienyl or 2-furyl subunits, R2 position must be free or occupied by a methyl group and R1 position must be free or occupied by Cl, CH3, OCH3 or CF3.
