Menoctone antimalarial

Quinones and naphthoquinones were explored during the World War 11 Antimalarial Dmg Program. Now that chloroquine resistance is a serious problem, compounds of this group such as menoctone (76) are being reinvestigated. 

The importance of naphthoquinones, particularly 2-hydroxy-3-alkyl-l,4-naphthoquinones, in chemotherapy of malaria came to light when a naphthoquinone, hydrolapachol (9), was found to possess activity against P. lophurai in ducks [8]. This observation prompted Fieser and coworkers [9-13] to synthesize a series of substituted naphthoquinones, of which lapinone (10) and menoctone (11) emerged as promising antimalarials. 

Hudson, A.T. Lapinone, menoctone, hydroxyquinolinequinones and similar structures. In Antimalarial Drugs volume II (Eds. Peters,W., Richards,W.H.G.), Springer-Verlag, Berlin, 1984, 343... 

The binding of 8-amlnoquinollne antlmalarials to DNA conqparable to that with chloroquine has been reported.7° effect on DNA fxmction may be involved with antimalarlal activity. Co-en nne Q which is associated with the mitochondrial oxidation of DPNH and succinate and is present in the metabolism of the parasite has been shown to be inhibited by chloroquine, primaquine, quinacrine and menoctone (IV), thus suggesting diversity of action for antimalarial drags.77... 

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