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ABSTRACT:
SUBMITTER: Zhang Y
PROVIDER: S-EPMC2788676 | biostudies-literature | 2009 Dec
REPOSITORIES: biostudies-literature
Zhang Yi Y Lee Yong Sok YS Rothman Richard B RB Dersch Christina M CM Deschamps Jeffrey R JR Jacobson Arthur E AE Rice Kenner C KC
Journal of medicinal chemistry 20091201 23
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 ...[more]