769919-91-7Relevant articles and documents
Potent antimalarial activity of 2-aminopyridinium salts, amidines, and guanidines
Calas, Michèle,Ouattara, Mahama,Piquet, Gilles,Ziora, Zyta,Bordat,Ancelin, Marie L.,Escale, Roger,Vial, Henri
, p. 6307 - 6315 (2007)
We describe the design, synthesis, and antimalarial activity of 60 bis-tertiary amine, bis-2(1H)-imino-heterocycle, bis-amidine, and bis-guanidine series. Bis-tertiary amines with a linker from 12 to 16 methylene groups were active against the in vitro growth of Plasmodium falciparum within the 10 -6-10-7 M concentration range. IC50 decreased by 2 orders of magnitude for bis-2-aminopyridinium salts, bis-amidines, and bis-guanidines (27 compounds with IC50 a over 12.5. Maximal activity occurs for bis-2-aminopyridinium, two C-duplicated bis-amidines, and three bis-guanidines, with IC50 values lower than 1 nM. In comparison to similar quaternary ammonium salts, amidinium compounds have distinct structural requirements for antimalarial activity and likely additional binding opportunities on account of their hydrogen-bond-forming properties.
