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

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• 作者：Malliga R. Iyer ; Yong Sok Lee ; Jeffrey R. Deschamps ; Richard B. Rothman ; Christina M. Dersch ; Arthur E. Jacobson ; Kenner C. Rice
• 关键词：Synthesis ; Opioid receptor binding ; N-substituted cis-4a-ethyl-1 ; 2 ; 3 ; 4 ; 4a ; 9a-hexahydrobenzofuro[2 ; 3-c]pyridin-8-ols ; Oxide-bridged phenylmorphans ; Geometry optimization ; Superposition
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2010
• 出版时间：1 January 2010
• 年：2010
• 卷：18
• 期：1
• 页码：91-99
• 全文大小：673 K

文摘

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 μ-opioid receptor affinity of the examined compounds (K_i = 0.35 μM).