Biomimetic in vitro oxidation of lapachol: A model to predict and analyse the in vivo phase I metabolism of bioactive compounds

…, VP Barros, F da Silva Emery, M Dias-Baruffi…

Index: Niehues, Michael; Barros, Valeria Priscila; Emery, Flavio Da Silva; Dias-Baruffi, Marcelo; Assis, Marilda Das Dores; Lopes, Norberto Peporine European Journal of Medicinal Chemistry, 2012 , vol. 54, p. 804 - 812

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Citation Number: 22

Abstract

The bioactive naphtoquinone lapachol was studied in vitro by a biomimetic model with Jacobsen catalyst (manganese (III) salen) and iodosylbenzene as oxidizing agent. Eleven oxidation derivatives were thus identified and two competitive oxidation pathways postulated. Similar to Mn (III) porphyrins, Jacobsen catalyst mainly induced the formation of para-naphtoquinone derivatives of lapachol, but also of two ortho-derivatives. The ...

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