Synthesis and antimalarial activity of (+)-deoxoartemisinin.
(+)-Deoxoartemisinin (2), a new and more active antimalarial agent, was successfully prepared from artemisinin in one step using NaBH4 and BF3.Et2O in THF. (-)-Deoxodeoxyartemisinin (5), a potential metabolite of deoxoartemisinin, was also prepared either from 2 or from artemisinic acid. 2 shows 8-fold increased antimalarial activity in vitro against chloroquine-resistant malaria as compared to artemisinin (1). Compound 2 possesses superior in vivo antimalarial activity to 1.
Jung
M
M
School of Pharmacy, University of Mississippi, University 38677.
Li
X
X
Bustos
D A
DA
elSohly
H N
HN
McChesney
J D
JD
Milhous
W K
WK
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis*; D037621:Artemisinins; D055598:Chemical Phenomena; D002621:Chemistry; D008288:Malaria / Q000188:drug therapy; D051379:Mice; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000962:Antimalarials; D037621:Artemisinins; D012717:Sesquiterpenes; C063801:deoxoartemisinin; C031327:artemisinin