(+/-)-cis-2-acetoxycyclobutyltrimethylammonium iodide: a semirigid analogue of acetylcholine.
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.
D000109:Acetylcholine / Q000031:analogs & derivatives*; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000494:pharmacology; D006168:Guinea Pigs; D066298:In Vitro Techniques; D007536:Isomerism; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D011976:Receptors, Muscarinic / Q000187:drug effects
D003503:Cyclobutanes; D011976:Receptors, Muscarinic; C035805:2-acetoxycyclobutyltrimethylammonium; D000109:Acetylcholine