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

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

Volume: 4 Issue: 5

Author(s): Joseph L. Kgokong, Gilbert M. Matsabisa, Peter P. Smith and Jaco C. Breytenbach

Affiliation:

Keywords: 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

Abstract: 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.

Cite this article as:

Kgokong L. Joseph, Matsabisa M. Gilbert, Smith P. Peter and Breytenbach C. Jaco, N,N-Bis(trifluoromethylquinolin-4-yl)diamino Alkanes: Synthesis and Antimalarial Activity, Medicinal Chemistry 2008; 4 (5) . https://dx.doi.org/10.2174/157340608785700216