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

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

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Former Faculty of Pharmaceutical Sciences

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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.

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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.",

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

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doi = "10.1016/j.bmcl.2008.11.011",

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AU - Hansen, Camilla Petrycer

AU - Jensen, Anders Asbjørn

AU - Balle, Thomas

AU - Bitsch-Jensen, Klaus

AU - Hassan, Mohamud M

AU - Liljefors, Tommy

AU - Frølund, Bente

N1 - Keywords: Carbachol; Carbamoylcholine (CCh); Carbamates; Humans; Nicotinic Agonists; Protein Binding; Receptors, Nicotinic; Structure-Activity Relationship;

PY - 2009

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N2 - 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.

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.

KW - Former Faculty of Pharmaceutical Sciences

U2 - 10.1016/j.bmcl.2008.11.011

DO - 10.1016/j.bmcl.2008.11.011

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JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

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ER -

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

Abstract

Keywords

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