Synthesis and antimalarial activity of febrifugine derivatives.
The regioisomers (2a,b) of the piperidine ring of febrifugine (1a) and isofebrifugine (1b) were synthesized from 4-allyl-3-piperidone (5). Reduction of 5 afforded a mixture of the trans and cis alcohols (6a,b) without diastereoselectivity; this result differentiated it from the reduction of 2-allyl-3-piperidone (14). The antimalarial activity of 2a,b and related compounds was tested.
Takeuchi
Y
Y
Faculty of Pharmaceutical Sciences, Okayama University, Japan. take@pharm.okayama-u.ac.jp
Koike
M
M
Azuma
K
K
Nishioka
H
H
Abe
H
H
Kim
H S
HS
Wataya
Y
Y
Harayama
T
T
D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010880:Piperidines; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000962:Antimalarials; D010880:Piperidines; D011799:Quinazolines; C001207:febrifugine