(+/-)-cis-2-acetoxycyclobutyltrimethylammonium iodide: a semirigid analogue of acetylcholine.


Journal Article

The title compound was prepared to complete a series of small ring (cyclopropane, cyclobutane) cis/trans 1,2-disubstituted 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-beta-methylcholine.

Full Text

Duke Authors

Cited Authors

  • Cannon, JG; Crockatt, DM; Long, JP; Maixner, W

Published Date

  • September 1982

Published In

Volume / Issue

  • 25 / 9

Start / End Page

  • 1091 - 1094

PubMed ID

  • 7131487

Pubmed Central ID

  • 7131487

International Standard Serial Number (ISSN)

  • 0022-2623

Digital Object Identifier (DOI)

  • 10.1021/jm00351a016


  • eng

Conference Location

  • United States