Issue 23, 2012
From the journal:

Organic & Biomolecular Chemistry

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

Riccardo Wanke,*a   David A. Novais,a   Shrika G. Harjivan,a   M. Matilde Marquesa  and  Alexandra M. M. Antunes*a  

* Corresponding authors

a Centro de Química Estrutural, Instituto Superior Técnico, Universidade Técnica de Lisboa, Lisboa, Portugal
E-mail: alexandra.antunes@ist.utl.pt, riccardowanke@ist.utl.pt
Fax: +351-21-8464455
Tel: +351-21-8417627

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 successful oxidation of the anti-estrogen tamoxifen and the equine estrogen equilin into their CYP-mediated metabolites supports the general application of bio-inspired nonheme Fe-complexes in mirroring CYP activity.

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

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Article information

DOI
https://doi.org/10.1039/C2OB25212K
Article type
Paper
Submitted
27 Jan 2012
Accepted
05 Apr 2012
First published
05 Apr 2012

Org. Biomol. Chem., 2012,10, 4554-4561

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

R. Wanke, D. A. Novais, S. G. Harjivan, M. M. Marques and A. M. M. Antunes, Org. Biomol. Chem., 2012, 10, 4554 DOI: 10.1039/C2OB25212K

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