A series of skeletal rearranged indolomorphinans 7a-d were obtained by N-demethylation of 3-methoxy-N-methyl-14-hydroxymorphinan-6-one 12 followed by N-realkylation, reduction and Fischer indole cyclization. The structure of the novel skeleton was confirmed by X-ray analysis. These new indoles displayed moderate binding affinity and selectivity at the μ receptor, with compound 7b showing the highest affinity at this receptor with a Ki value of 40 nM, and 6- and 25-fold selectivity against δ and κ receptors, respectively. Function assays showed that indolopropellanes 7b and 7c possessed full agonistic activity at all the opioid receptors indicating a different interaction model existed. © 2009 Elsevier Ltd. All rights reserved.
CITATION STYLE
Li, F., Gaob, L., Yin, C., Chen, J., Liu, J., Xie, X., & Zhang, A. (2009). Synthesis and opioid receptor activity of indolopropellanes. Bioorganic and Medicinal Chemistry Letters, 19(16), 4603–4606. https://doi.org/10.1016/j.bmcl.2009.06.093
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