Probes for narcotic receptor mediated phenomena. 39. Enantiomeric N-substituted benzofuro[2,3-c]pyridin-6-ols: synthesis and topological relationship to oxide-bridged phenylmorphans.

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Zhang Y, Lee YS, Rothman RB, Dersch CM, Deschamps JR, Jacobson AE, Rice KC

Probes for narcotic receptor mediated phenomena. 39. Enantiomeric N-substituted benzofuro[2,3-c]pyridin-6-ols: synthesis and topological relationship to oxide-bridged phenylmorphans.

J Med Chem. 2009 Dec 10;52(23):7570-9. doi: 10.1021/jm9004225.

PubMed ID

19627147 [ View in PubMed

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Abstract

Enantiomers of N-substituted benzofuro[2,3-c]pyridin-6-ols have been synthesized, and the subnanomolar affinity and potent agonist activity of the known racemic N-phenethyl substituted benzofuro[2,3-c]pyridin-6-ol can now be ascribed to the 4aS,9aR enantiomer. The energy-minimized structures suggest that the active enantiomer bears a greater three-dimensional resemblance to morphine than to an ostensibly structurally similar oxide-bridged phenylmorphan. Structural features of the conformers of N-substituted benzofuro[2,3-c]pyridin-6-ols were compared to provide the rationale for their binding affinity.

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Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Morphine	Mu-type opioid receptor	Ki (nM)	2.55	N/A	N/A	Details