(±)-cis-2-acetoxycyclobutyltrimethylammonium iodide: A semirigid analogue of acetylcholine

Joseph G. Cannon, Dale M. Crockatt, John Paul Long, William Maixner

Research output: Research - peer-reviewArticle

  • 5 Citations

Abstract

The title compound was prepared to complete a series of small ring (cyclopropane, cyclobutane) cis/trans 1,2-di-substituted semirigid congeners of acetylcholine. A multistep synthetic sequence, beginning with cis-cyclobutane-1,2-dicarboxylic anhydride, permitted unequivocal preparation of the (±)-cis target compound 4. The geometry of 4 was confirmed by comparison with an authentic sample of the (±)-trans isomer. The cis and trans isomers were equipotent as muscarinic agonists, but they were much weaker than acetyl-β-methylcholine.

LanguageEnglish (US)
Pages1091-1094
Number of pages4
JournalJournal of Medicinal Chemistry
Volume25
Issue number9
StatePublished - 1982
Externally publishedYes

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Cyclobutanes
Isomers
Acetylcholine
2-acetoxycyclobutyltrimethylammonium
Muscarinic Agonists
Methacholine Chloride
Anhydrides
Geometry
cyclopropane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

(±)-cis-2-acetoxycyclobutyltrimethylammonium iodide : A semirigid analogue of acetylcholine. / Cannon, Joseph G.; Crockatt, Dale M.; Long, John Paul; Maixner, William.

In: Journal of Medicinal Chemistry, Vol. 25, No. 9, 1982, p. 1091-1094.

Research output: Research - peer-reviewArticle

Cannon, Joseph G. ; Crockatt, Dale M. ; Long, John Paul ; Maixner, William. / (±)-cis-2-acetoxycyclobutyltrimethylammonium iodide : A semirigid analogue of acetylcholine. In: Journal of Medicinal Chemistry. 1982 ; Vol. 25, No. 9. pp. 1091-1094
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