Carbamoylcholine analogs as nicotinic acetylcholine receptor agonists--structural modifications of 3-(dimethylamino)butyl dimethylcarbamate (DMABC)

Research output: Contribution to journalJournal articleResearchpeer-review

Camilla Petrycer Hansen, Anders Asbjørn Jensen, Thomas Balle, Klaus Bitsch-Jensen, Mohamud M Hassan, Tommy Liljefors, Bente Frølund

Compounds based on the 3-(dimethylamino)butyl dimethylcarbamate (DMABC) scaffold were synthesized and pharmacologically characterized at the alpha(4)beta(2), alpha(3)beta(4,) alpha(4)beta(4) and alpha(7) neuronal nicotinic acetylcholine receptors (nAChRs). The carbamate functionality and a small hydrophobic substituent in the C-3 position were found to be vital for the binding affinity to the nAChRs, whereas the carbamate nitrogen substituents were important for nAChR subtype selectivity. Finally, the compounds were found to be agonists at the alpha(3)beta(4) nAChR.
Original languageEnglish
JournalBioorganic & Medicinal Chemistry Letters
Volume19
Issue number1
Pages (from-to)87-91
ISSN0960-894X
DOIs
Publication statusPublished - 2009

Bibliographical note

Keywords: Carbachol; Carbamoylcholine (CCh); Carbamates; Humans; Nicotinic Agonists; Protein Binding; Receptors, Nicotinic; Structure-Activity Relationship;

ID: 10246464