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.
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA. pwipf@pitt.edu
Peter
P
Wipf
Tingting
T
Mo
Steven J
SJ
Geib
Diana
D
Caridha
Geoffrey S
GS
Dow
Lucia
L
Gerena
Norma
N
Roncal
Erin E
EE
Milner
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