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In vivo antimalarial activity of novel 2-hydroxy-3-anilino-1,4-naphthoquinones obtained by epoxide ring-opening reaction

1,4-Naphthoquinones are a class of compounds broadly studied in organic synthesis, medicinal chemistry and natural products chemistry. 1 Within these studies, the antimalarial activity has been widely reported for several 1,4-naphthoquinones. 2 The antiparasitic activity of the quinones is related to several mechanisms such as the competitive inhibition of the cytochrome bc1 complex, generation of reactive oxygen species, enzymatic inhibition (e.g., glutathione reductase, dihydroorotate dehydrogenase and glycerol glyceraldehyde-3-phosphate dehydrogenase) alkylation of biomolecules, depletion of glutathione, among others. 3 </P>Lawsone derivatives containing the 2-hydroxy-1,4-naphthoquinone scaffold are highly explored for the development of novel antiparasitics. Atovaquone, parvaquone and buparvaquone are 3-substituted-2-hydroxy-1,4-naphthoquinones clinically applied as antimalarial (atovaquone) and antipneumocystic (parvaquone and buparvaquone) agents, which exemplifies the potentiality of such scaffold in the development of novel drugs. Additionally, some studies indicate the potential application of natural or synthetic 2-amino-1,4-naphthoquinones and 2-amino-1,2-naphthoquinones as antiplasmodial agents. 4 </P>Despite the pharmacological relevance of aminated and hydroxylated naphthoquinoidal derivatives and the wide structural diversity of 1,4-naphthoquinones, 2-amino-3-hydroxy-1,4-naphthoquinone is an uncommon structural fragment only observed in few examples of natural products and bioactive compounds. 5 Recently 2-(4-phenylpiperazinyl)-3-hydroxy-1,4-naphthoquinone 1 , 6 which can be seen as a ring bioisostere of atovaquone, was shown to have inhibitory effects against http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Bioorganic & Medicinal Chemistry Letters Elsevier
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