- 1,4-naphthoquinone cations as antiplasmodial agents: Hydroxy-, acyloxy-, and alkoxy-substituted analogues
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Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4-49.5 nM against heteroresistant P. falciparum W2.
- Lu, Xiao,Altharawi, Ali,Gut, Jiri,Rosenthal, Philip J.,Long, Timothy E.
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supporting information
p. 1029 - 1033
(2013/02/22)
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- Allylation of Quinones via Photoinduced Electron-Transfer Reactions from Allylstannanes
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Photochemical reactions of quinones with allylstannanes provided four types of products: adducts of allyl group to the carbonyl oxygens of quinones, adducts of allyl group to the olefinic carbons, adducts of allyl group to the carbonyl carbons, and hydroquinones.An electron-transfer mechanism was confirmed by 1H-CIDNP (Chemically Induced Dynamic Nuclear Polarization) method.This study suggests that a) photoinduced electron transfer from allylstannanes to quinones produces the corresponding quinone anion radicals and tin cation radicals, b) the tin cation radicals cleave to give allyl radicals as well as tin cation, and c) the allyl radicals attack the quinone anion radicals resulting in the formation of final products, allylated quinones.
- Maruyama, Kazuhiro,Imahori, Hiroshi
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p. 816 - 825
(2007/10/02)
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