Amidomethylation of amodiaquine: antimalarial N-Mannich base derivatives

Lopes, Francisca; Capela, Rita; Gonçaves, Jose O.; Horton, Peter N.; Hursthouse, Michael B.; Iley, Jim; Casimiro, Catarina M.; Bom, Joana and Moreira, Rui (2004). Amidomethylation of amodiaquine: antimalarial N-Mannich base derivatives. Tetrahedron Letters, 45(41) 7663 -7666.



Novel N-Mannich base-type derivatives of the antimalarial drug amodiaquine were synthesised by reaction with tertiary N-chloromethylamides. With the exception of the derivative of ethyl hippurate, all the so-formed (1-amidomethyl-1H-quinolin-4-ylidene)arylamines displayed high chemical and enzymatic stability. These compounds displayed antimalarial activity against the multi-drug resistant Plasmodium falciparum strain Dd2 (IC50 values 15–31nM) and demonstrated no significant loss in activity compared to amodiaquine (IC50 30nM).

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