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

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1813-1818
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume8
Issue number14
DOIs
Publication statusPublished - Jul 21 1998
Externally publishedYes

Fingerprint

Morphine
Opioid Analgesics
Conformations
Ligands
Binders
benzofuran
piperidine
4-methylpiperidine
N-methylpiperidine

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

C-alkylated spiro[benzofuran-3(2H),4'-1'-methyl-piperidine-7-ols] as potent opioids : A conformation-activity study. / Tsai, Ya Ching; Liou, Jing Ping; Liao, Richard; Cheng, Chen Yu; Tao, Pao Luh.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 8, No. 14, 21.07.1998, p. 1813-1818.

Research output: Contribution to journalArticle

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