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N,N-Bis(trifluoromethylquinolin-4-yl)diamino Alkanes: Synthesis and Antimalarial Activity

[ Vol. 4 , Issue. 5 ]


Joseph L. Kgokong, Gilbert M. Matsabisa, Peter P. Smith and Jaco C. Breytenbach   Pages 438 - 445 ( 8 )


A series of N,N-bis(trifluoromethylquinolin-4-yl)- and N,N-bis[2,8-bis(trifluoromethyl)quinolin-4-yl] diamino alkane and piperazine derivatives were synthesised by employing a simple and rapid displacement reaction of the 4-chloro group on the 2-trifluoromethyl- and 2,8-bis(trifluoromethyl)-quinoline by diaminoalkane or piperazine groups. Results of in vitro antimalarial activity evaluations of these compounds against the chloroquine-sensitive (D10) and chloroquineresistant (K1) strains of Plasmodium falciparum indicate that compounds with trifluoromethyl groups in both the 2 and 8 positions coupled with diaminoalkyl bridging chains of 2 to 6 carbon atoms exhibit a slightly higher activity than compound with only a trifluoromethyl group at position 2, and those with a piperazine bridge These compounds exhibit higher activity in the chloroquine-resistant than in the chloroquine-sensitive strains of the Plasmodium. Comparative studies indicate that the compounds are more selective in their cytotoxicity against the parasite cells. Except for compounds containing a piperazine bridge, this new series of compounds interact with ferriprotoporphyrin IX to more or less the same extent.


N,N-Bis(Trifluoromethylquinolin-4-yl)diamino alkanes, N,N-bis[2,8-bis(trifluoromethyl)quinolin-4-yl]diamino alkanes, antimalarial activity, synthesis, Ferriprotoporphyrin IX, cytotoxicity


Medicines Regulatory Affairs, National Department of Health, Private Bag X828, Pretoria. 0001. South Africa.

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