C-alkylated spiro[benzofuran-3(2H),4'-1'-methyl-piperidine-7-ols] as potent opioids: A conformation-activity study

Ya Ching Tsai, Jing Ping Liou, Richard Liao, Chen Yu Cheng, Pao Luh Tao

研究成果: 雜誌貢獻文章同行評審

10 引文 斯高帕斯(Scopus)

摘要

Among a series of C-alkylated analogs of the weak μ opioid ligand spiro[benzofuran-3(2H),4'-1'-methylpiperidine-7-ol] (1), the 2-methyl, 2- ethyl, and cis 3'-methyl analogs, namely compounds (±)2, (±)-3, and (±)- 4, showed much enhanced μ-affinities, with (±)-4 being almost as potent as (-)-morphine; while the trans 3'-methyl analog (±)-5 remained a weak μ- binder. Energy calculations and nmr data indicated that compounds 2-4 favor phenyl-axial conformations, while compounds 1 and 5 favor phenyl-equatorial conformations.

原文英語
頁(從 - 到)1813-1818
頁數6
期刊Bioorganic and Medicinal Chemistry Letters
8
發行號14
DOIs
出版狀態已發佈 - 7月 21 1998
對外發佈

ASJC Scopus subject areas

  • 生物化學
  • 分子生物學
  • 有機化學
  • 藥物發現
  • 藥學科學

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