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

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

doi:10.1016/j.bmcl.2008.11.011

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

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

Research output: Contribution to journal › Journal article › Research › peer-review

5 Citations (Scopus)

Abstract

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 language	English
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	19
Issue number	1
Pages (from-to)	87-91
ISSN	0960-894X
DOIs	https://doi.org/10.1016/j.bmcl.2008.11.011
Publication status	Published - 2009

Bibliographical note

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

Keywords

Former Faculty of Pharmaceutical Sciences

Access to Document

10.1016/j.bmcl.2008.11.011

Cite this

Carbamoylcholine analogs as nicotinic acetylcholine receptor agonists--structural modifications of 3-(dimethylamino)butyl dimethylcarbamate (DMABC). / Hansen, Camilla Petrycer; Jensen, Anders Asbjørn; Balle, Thomas et al.
In: Bioorganic & Medicinal Chemistry Letters, Vol. 19, No. 1, 2009, p. 87-91.

Research output: Contribution to journal › Journal article › Research › peer-review

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AU - Bitsch-Jensen, Klaus

AU - Hassan, Mohamud M

AU - Liljefors, Tommy

AU - Frølund, Bente

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AB - 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.

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