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Structural optimization of quinolon-4(1H)-imines as dual-stage antimalarials: toward increased potency and metabolic stability.

Abstract：

:Discovery of novel effective and safe antimalarials has been traditionally focused on targeting erythrocytic parasite stages that cause clinical symptoms. However, elimination of malaria parasites from the human population will be facilitated by intervention at different life-cycle stages of the parasite, including the obligatory developmental phase in the liver, which precedes the erythrocytic stage. We have previously reported that N-Mannich-based quinolon-4(1H)-imines are potent antiplasmodial agents but present several stability liabilities. We now report our efforts to optimize quinolon-4(1H)-imines as dual-stage antiplasmodial agents endowed with chemical and metabolic stability. We report compounds active against both the erythrocytic and exoerythrocytic forms of malaria parasites, such as the quinolon-4(1H)-imine 5p (IC50 values of 54 and 710 nM against the erythrocytic and exoerythrocytic forms), which constitute excellent starting points for further lead optimization as dual-stage antimalarials.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Ressurreição AS,Gonçalves D,Sitoe AR,Albuquerque IS,Gut J,Góis A,Gonçalves LM,Bronze MR,Hanscheid T,Biagini GA,Rosenthal PJ,Prudêncio M,O'Neill P,Mota MM,Lopes F,Moreira R

doi

10.1021/jm4011466

subject

Has Abstract

pub_date

2013-10-10 00:00:00

pages

7679-90

issue

19

eissn

0022-2623

issn

1520-4804

journal_volume

56

pub_type

杂志文章

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