Stereochemical Studies on Medicinal Agents. 9.1Bicyclic Bases. Synthesis and Biological Activities of Epimeric Quaternary Derivatives of 2-Oxa-5-azabicyclo[2.2.1]heptane

Philip S Portoghese, J. G. Tijrcotte

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Abstract

Optically active N-Me-N-benzyl quaternary derivatives of (1S,2S)-2-oxa-5-azabicyclo[2.2.1]heptane were synthesized in order to investigate the effect of an asymmetric quaternary N on anticholinergic activity. Nmr studies indicate that the N-substituted bicyclic system undergoes highly stereoselective quaternization. Configurations have been tentatively assigned to the N epimers. The exo-5-methyl-crido-5-benzyl and ero-5-benzyl-endo-5-methyl N epimers possess comparable antagonistic activities on the guinea pig ileum. The possible implications of the biological data are discussed.

Original languageEnglish (US)
Pages (from-to)288-291
Number of pages4
JournalJournal of Medicinal Chemistry
Volume14
Issue number4
DOIs
StatePublished - Apr 1 1971

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Heptanes
Cholinergic Antagonists
Ileum
Guinea Pigs

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title = "Stereochemical Studies on Medicinal Agents. 9.1Bicyclic Bases. Synthesis and Biological Activities of Epimeric Quaternary Derivatives of 2-Oxa-5-azabicyclo[2.2.1]heptane",
abstract = "Optically active N-Me-N-benzyl quaternary derivatives of (1S,2S)-2-oxa-5-azabicyclo[2.2.1]heptane were synthesized in order to investigate the effect of an asymmetric quaternary N on anticholinergic activity. Nmr studies indicate that the N-substituted bicyclic system undergoes highly stereoselective quaternization. Configurations have been tentatively assigned to the N epimers. The exo-5-methyl-crido-5-benzyl and ero-5-benzyl-endo-5-methyl N epimers possess comparable antagonistic activities on the guinea pig ileum. The possible implications of the biological data are discussed.",
author = "Portoghese, {Philip S} and Tijrcotte, {J. G.}",
year = "1971",
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language = "English (US)",
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journal = "Journal of Medicinal Chemistry",
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T1 - Stereochemical Studies on Medicinal Agents. 9.1Bicyclic Bases. Synthesis and Biological Activities of Epimeric Quaternary Derivatives of 2-Oxa-5-azabicyclo[2.2.1]heptane

AU - Portoghese, Philip S

AU - Tijrcotte, J. G.

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N2 - Optically active N-Me-N-benzyl quaternary derivatives of (1S,2S)-2-oxa-5-azabicyclo[2.2.1]heptane were synthesized in order to investigate the effect of an asymmetric quaternary N on anticholinergic activity. Nmr studies indicate that the N-substituted bicyclic system undergoes highly stereoselective quaternization. Configurations have been tentatively assigned to the N epimers. The exo-5-methyl-crido-5-benzyl and ero-5-benzyl-endo-5-methyl N epimers possess comparable antagonistic activities on the guinea pig ileum. The possible implications of the biological data are discussed.

AB - Optically active N-Me-N-benzyl quaternary derivatives of (1S,2S)-2-oxa-5-azabicyclo[2.2.1]heptane were synthesized in order to investigate the effect of an asymmetric quaternary N on anticholinergic activity. Nmr studies indicate that the N-substituted bicyclic system undergoes highly stereoselective quaternization. Configurations have been tentatively assigned to the N epimers. The exo-5-methyl-crido-5-benzyl and ero-5-benzyl-endo-5-methyl N epimers possess comparable antagonistic activities on the guinea pig ileum. The possible implications of the biological data are discussed.

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