Benzofuro[2,3-c]pyridinols are partial structures of oxide-bridged phenylmorphans. Racemic cis-benzofuro[2,3-c]pyridin-6-ol with a phenethyl substituent on nitrogen and a C4a ethyl substituent 1 have  been shown by Hutchison, et al. to have a high affinity for opioid receptors. As part of our continuing interest in benzofuro[2,3-c]pyridin-ol series of compounds, we have devised a simpler route for the synthesis of these compounds. This route enabled the studies on heretofore, unexplored analogs in the racemic cis-benzofuro[2,3-c]pyridin-6-ol series of compounds. A study involving the effect of chain length and substitution at the C4a position of cis-hexahydrobenzofuro[2,3-c]pyridin-6-ols was undertaken. The N-methyl-C4a-alkyl 2 and ar-alkyl 3 derivatives were synthesized and their affinity on opioid receptors was determined. Binding studies and functional assays revealed interesting trends. Data from this study will be discussed. Additional manipulations were made to modify the N-substitution. Synthesis and binding studies of the C4a phenethyl N-substituted derivatives 4 will also be presented.

Probes for narcotic receptor mediated phenomena: Effect of C4a ar-alkyl and alkyl chain length on the opioid receptor affinity of N-methyl cis-4a-substituted 1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols

242nd National Meeting (2011)

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