New syntheses and potential antimalarial activities of new 'retinoid-like chalcones'.
A series of 'retinoid-like chalcones' and diverse derivatives relative to licochalcone A were synthesized from a new enaminone synthon. These syntheses occurred via a new aromatic annelation. These new derivatives have been tested in vitro as potential antimalarial agents. The 4-hydroxy-chalcone-like (compound 6a, derived from beta-ionone) exhibits a good and reproducible inhibitory effect on the in vitro culture of Plasmodium falciparum, with an IC 50 lower than 10 microM for inhibition of 3H-hypoxanthine uptake by parasites (respectively, 4.93 and 8.47 microM for strains K1 and Thaï).
Valla
Alain
A
CNRS, FRE 2125, 6, rue de l'université, 29000 Quimper, France. alain.valla@cegetel.net
Valla
Benoist
B
Cartier
Dominique
D
Le Guillou
Régis
R
Labia
Roger
R
Florent
Loic
L
Charneau
Sébastien
S
Schrevel
Joseph
J
Potier
Pierre
P
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002599:Chalcone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D004912:Erythrocytes / Q000469:parasitology*; D006801:Humans; D020128:Inhibitory Concentration 50; D008288:Malaria / Q000097:blood / Q000188:drug therapy / Q000469:parasitology; D018512:Parasitemia / Q000188:drug therapy; D010963:Plasmodium falciparum / Q000187:drug effects* / Q000254:growth & development / Q000378:metabolism; D012176:Retinoids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000962:Antimalarials; D012176:Retinoids; D002599:Chalcone