Section 56
Chapter 55,190

Probes for narcotic receptor mediated phenomena. 40. N-substituted cis-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-8-ols

Iyer, M.R.; Lee, Y.S.; Deschamps, J.R.; Rothman, R.B.; Dersch, C.M.; Jacobson, A.E.; Rice, K.C.

Bioorganic and Medicinal Chemistry 18(1): 91-99


ISSN/ISBN: 1464-3391
PMID: 20005115
DOI: 10.1016/j.bmc.2009.11.022
Accession: 055189653

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A series of N-substituted rac-cis-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-8-ols have been prepared using a simple synthetic route previously designed for synthesis of related cis-2-methyl-4a-alkyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols. The new phenolic compounds, where the aromatic hydroxy moiety is situated ortho to the oxygen atom in the oxide-bridged ring, do not interact as well as the pyridin-6-ols with opioid receptors. The N-para-fluorophenethyl derivative had the highest mu-opioid receptor affinity of the examined compounds (K(i)=0.35 microM).

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