First synthesis of 10 alpha-(trifluoromethyl)deoxoartemisinin.
[reaction: see text] A novel, nonacetal (trifluoromethyl)deoxoartemisinin was prepared with good stereoselectivity. This compound was obtained by debromination of the 10 alpha-CF3-10-bromodeoxoartemisinin in the presence of tributyltin hydride at reflux in toluene without alteration of the endoperoxide bridge. It presented a reasonable antimalarial activity.
Chorki
Fatima
F
BioCIS, Centre d'Etudes Pharmaceutiques, rue J.B. Clément, Châtenay-Malabry F-92296 Cedex, France.
Grellepois
Fabienne
F
Crousse
Benoit
B
Hoang
Vu Dinh
VD
Hung
Nguyen Van
NV
Bonnet-Delpon
Danièle
D
Bégué
Jean-Pierre
JP
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology; D019306:Artemisia / Q000737:chemistry; D037621:Artemisinins / Q000138:chemical synthesis* / Q000494:pharmacology; D004351:Drug Resistance; D006219:Halogens / Q000737:chemistry; D020128:Inhibitory Concentration 50; D010963:Plasmodium falciparum / Q000187:drug effects; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
C467073:10-(trifluoromethyl)deoxoartemisinin; D000962:Antimalarials; D037621:Artemisinins; D006219:Halogens; D012717:Sesquiterpenes; C031327:artemisinin