3-Deoxyclocinnamox

The first high-affinity, nonpeptide μ-opioid antagonist lacking a phenolic hydroxyl group

I. Derrick, C. L. Neilan, J. Andes, S. M. Husbands, J. H. Woods, J. R. Traynor, J. W. Lewis

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The C3-substituent in morphinan opioids is of critical importance; the 3-OH group is usually associated with very much higher affinity for μ-receptors than H or -OMe. However in this series of 14β-cinnamoylamino derivatives the codeinones (e.g. methoclocinnamox, MC-CAM) had unexpectedly high μ-opioid receptor affinity, similar to that of the morphinone (clocinnamox, C-CAM). The current report relates to the synthesis and in vitro evaluation of deoxyclocinnamox (DOC-CAM) which acted as a high-affinity opioid antagonist similar to C-CAM but with greater μ selectivity. Thus it appears that the C3-substituent does not play a major role in the binding of the 14β-cinnamoyl series and that the cinnamoyl group itself may in fact be the dominant binding feature.

Original languageEnglish
Pages (from-to)3348-3350
Number of pages3
JournalJournal of Medicinal Chemistry
Volume43
Issue number17
DOIs
Publication statusPublished - 1 Aug 2000

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

3-Deoxyclocinnamox : The first high-affinity, nonpeptide μ-opioid antagonist lacking a phenolic hydroxyl group. / Derrick, I.; Neilan, C. L.; Andes, J.; Husbands, S. M.; Woods, J. H.; Traynor, J. R.; Lewis, J. W.

In: Journal of Medicinal Chemistry, Vol. 43, No. 17, 01.08.2000, p. 3348-3350.

Research output: Contribution to journalArticle

Derrick, I. ; Neilan, C. L. ; Andes, J. ; Husbands, S. M. ; Woods, J. H. ; Traynor, J. R. ; Lewis, J. W. / 3-Deoxyclocinnamox : The first high-affinity, nonpeptide μ-opioid antagonist lacking a phenolic hydroxyl group. In: Journal of Medicinal Chemistry. 2000 ; Vol. 43, No. 17. pp. 3348-3350.
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AU - Woods, J. H.

AU - Traynor, J. R.

AU - Lewis, J. W.

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