Biomimetic oxidation of aromatic xenobiotics: synthesis of the phenolic metabolites from the anti-HIV drug efavirenz

…, SG Harjivan, MM Marques, AMM Antunes

Index: Wanke, Riccardo; Novais, David A.; Harjivan, Shrika G.; Marques, M. Matilde; Antunes, Alexandra M. M. Organic and Biomolecular Chemistry, 2012 , vol. 10, # 23 p. 4554 - 4561

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Citation Number: 3

Abstract

We report the oxidation of the first line anti-HIV drug efavirenz (EFV), mediated by a bio- inspired nonheme Fe-complex. Depending upon the experimental conditions this system can be tuned either to yield the major EFV metabolite, 8-hydroxy-EFV, in enantiomerically pure form or to mimic cytochrome P450 (CYP) activity, yielding 8-hydroxy-EFV and 7- hydroxy-EFV, the two phenolic EFV metabolites reported to be formed in vivo. The ...