Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 23, 2012
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation
Please wait while Download options loads

Publication details

The article was received on 27 Jan 2012, accepted on 05 Apr 2012 and first published on 05 Apr 2012


Article type: Paper
DOI: 10.1039/C2OB25212K
Citation: Org. Biomol. Chem., 2012,10, 4554-4561
  •   Request permissions

    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

Search articles by author