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. 2008 Jan 15;16(2):869-73.
doi: 10.1016/j.bmc.2007.10.030. Epub 2007 Oct 13.

The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans

Matthew D Metcalf  1 , Mario D Aceto, Louis S Harris, James H Woods, John R Traynor, Andrew Coop, Everette L May
Affiliations

The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans

Matthew D Metcalf et al. Bioorg Med Chem. .

Abstract

To investigate the effects of carboxylic ester and acid moieties as the N-substituent of opioids, a short series of racemic N-substituted normetazocines was prepared. The introduction of both groups as the normetazocine N-substituent produced compounds which displayed low potency in vitro and in vivo, with the esters displaying the greater activity. The pharmacology of the compounds is discussed with implications resulting from potential in vivo metabolic hydrolysis.

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Figures

Scheme 1
Scheme 1
Reagents and conditions: a. DMF/THF, K2CO3, reflux 3–6 h; b. EtOH, H2O, KOH, reflux 1–2 h.
See this image and copyright information in PMC

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