Piperidine dispiro-1,2,4-trioxane analogues.
Dispiro N-Boc-protected 1,2,4-trioxane 2 was synthesised via Mo(acac)(2) catalysed perhydrolysis of N-Boc spirooxirane followed by condensation of the resulting beta-hydroperoxy alcohol 10 with 2-adamantanone. N-Boc 1,2,4-trioxane 2 was converted to the amine 1,2,4-trioxane hydrochloride salt 3 which was subsequently used to prepare derivatives (4-7). Several of these novel 1,2,4-trioxanes had nanomolar antimalarial activity versus the 3D7 strain of Plasmodium falciparum. Amine intermediate 3 represents a versatile derivative for the preparation of achiral arrays of trioxane analogues with antimalarial activity.
Sabbani
Sunil
S
Department of Natural Sciences, Mid Sweden University, SE-85170 Sundsvall, Sweden.
Stocks
Paul A
PA
Ellis
Gemma L
GL
Davies
Jill
J
Hedenstrom
Erik
E
Ward
Stephen A
SA
O'Neill
Paul M
PM
D000818:Animals; D000962:Antimalarials / Q000737:chemistry* / Q000494:pharmacology; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010880:Piperidines / Q000737:chemistry* / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects
D000962:Antimalarials; D010880:Piperidines