Bicyclo[2.2.2]octyl esters of dialkylamino acids as antiprotozoals.
A couple of bicyclo[2.2.2]octyl esters of 2-dialkylaminoacetic acids were prepared. Their antiplasmodial and antitrypanosomal activities against Trypanosoma brucei rhodesiense (STIB 900) and the K(1) strain of Plasmodium falciparum (resistant to chloroquine and pyrimethamine) were determined using microplate assays. Structure-activity relationships were discussed. The antiprotozoal activities were remarkably increased by insertion of a second basic centre. The selectivity indices of the most active compounds are superior in the bicyclo-octane series.
Schlapper
Christian
C
Institute of Pharmaceutical Sciences, Pharmaceutical Chemistry, Karl-Franzens-University, Universitätsplatz 1, A-8010 Graz, Austria.
Seebacher
Werner
W
Kaiser
Marcel
M
Brun
Reto
R
Saf
Robert
R
Weis
Robert
R
D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry*; D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry* / Q000633:toxicity*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000187:drug effects; D013329:Structure-Activity Relationship; D016833:Trypanosoma brucei rhodesiense / Q000187:drug effects
D000596:Amino Acids; D000981:Antiprotozoal Agents; D001643:Bridged Bicyclo Compounds; D004952:Esters