A concise silylamine approach to 2-amino-3-hydroxy-indoles with potent in vivo antimalaria activity.
The development of a concise strategy to access 2-amino-3-hydroxy-indoles, which are disclosed as novel antimalarials with potent in vivo activity, is reported. Starting from isatins the target compounds are synthesized in 2 steps and in good yields via oxoindole intermediates by employing tert-butyldimethylsilyl amine (TBDMSNH(2)) as previously unexplored ammonia equivalent.
Urgaonkar
Sameer
S
Infectious Disease Initiative Program, The Broad Institute of Harvard and MIT, 7 Cambridge Center, Cambridge, Massachusetts 02142, USA.
Cortese
Joseph F
JF
Barker
Robert H
RH
Cromwell
Mandy
M
Serrano
Adelfa E
AE
Wirth
Dyann F
DF
Clardy
Jon
J
Mazitschek
Ralph
R
D000588:Amines / Q000737:chemistry*; D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000627:therapeutic use*; D007211:Indoles / Q000138:chemical synthesis* / Q000627:therapeutic use; D016778:Malaria, Falciparum / Q000188:drug therapy*; D051379:Mice; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000187:drug effects; D012821:Silanes / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000588:Amines; D000962:Antimalarials; D007211:Indoles; D012821:Silanes; C510549:3-hydroxyindole