Novel spiroanellated 1,2,4-trioxanes with high in vitro antimalarial activities.
A remarkable increase in antimalarial in vitro activity was achieved by integration of spiroadamantane motifs in 6-alkylidene 1,2,4-trioxanes 3a-h via diastereoselective photooxygenation of allylic alcohols and subsequent BF(3)-catalyzed peroxyacetalization with adamantanone to give the active compounds 3e-h.
Griesbeck
Axel G
AG
Institut für Organische Chemie, Universität zu Köln, Greinstr. 4, D-50939 Köln, Germany. griesbeck@uni-koeln.de
El-Idreesy
Tamer T
TT
Höinck
Lars-Oliver
LO
Lex
Johann
J
Brun
Reto
R
D000218:Adamantane / Q000737:chemistry; D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology; D016923:Cell Death / Q000187:drug effects; D002460:Cell Line; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000187:drug effects; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000962:Antimalarials; D006571:Heterocyclic Compounds; D013141:Spiro Compounds; C011374:s-trioxane; D000218:Adamantane