Is nevirapine atropisomeric? Experimental and computational evidence for rapid conformational inversion

Edmund W D Burke, Gareth A. Morris, Mark A. Vincent, Ian H. Hillier, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

9 Citations (Scopus)

Abstract

The non-nucleoside reverse transcriptase inhibitor nevirapine displays in its room temperature 1H-NMR spectrum signals characteristic of a chiral compound. Following suggestions in the recent literature that nevirapine may display atropisomerism - and therefore be a chiral compound, due to slow interconversion between two enantiomeric conformers - we report the results of an NMR and computational study which reveal that while nevirapine does indeed possess two stable enantiomeric conformations, they interconvert with a barrier of about 76 kJ mol -1 at room temperature. Nevirapine has a half life for enantiomerisation at room temperature of the order of seconds, is not atropisomeric, and cannot exist as separable enantiomers.

Original languageEnglish
Pages (from-to)716-719
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number4
Early online date22 Nov 2011
DOIs
Publication statusPublished - 28 Jan 2012

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