Synthesis and biological evaluation of the first pentafluorosulfanyl analogs of mefloquine.
Two novel SF5 analogs of the antimalarial agent mefloquine were synthesized in 5 steps and 10-23% overall yields and found to have improved activity and selectivity against malaria parasites. This work also represents the first report of SF5-substituted quinolines.
Wipf
Peter
P
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA. pwipf@pitt.edu
Mo
Tingting
T
Geib
Steven J
SJ
Caridha
Diana
D
Dow
Geoffrey S
GS
Gerena
Lucia
L
Roncal
Norma
N
Milner
Erin E
EE
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D015767:Mefloquine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D008958:Models, Molecular; D008968:Molecular Conformation; D010963:Plasmodium falciparum / Q000187:drug effects
D000962:Antimalarials; D015767:Mefloquine