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The 3,7-diazabicyclo[3.3.1]nonane Scaffold for Subtype Selective Nicotinic Acetylcholine Receptor Ligands. Part 2: Carboxamide Derivatives With Different Spacer Motifs

The 3,7-diazabicyclo[3.3.1]nonane Scaffold for Subtype Selective Nicotinic Acetylcholine Receptor Ligands. Part 2: Carboxamide Derivatives With Different Spacer Motifs

Christoph Eibl, Lenka Munoz, Isabelle Tomassoli, Clare Stokes, Roger L Papke, Daniela Gündisch

Bioorg Med Chem. 2013 Dec 1;21(23):7309-29.

PMID: 24145137

Abstract:

3,7-Diazabicyclo[3.3.1]nonane (bispidine) based nicotinic acetylcholine receptor (nAChR) ligands have been synthesized and evaluated for nAChRs interaction. Diverse spacer motifs were incorporated between the hydrogen bond acceptor (HBA) part and a variety of substituted (hetero)aryl moieties. Bispidine carboxamides bearing spacer motifs often showed high affinity in the low nanomolar range and selectivity for the α4β2(∗) nAChR. Compounds 15, 25, and 47 with Ki values of about 1 nM displayed the highest affinities for α4β2(∗) nAChR. All evaluated compounds are partial agonists or antagonists at α4β2(∗), with reduced or no effects on α3β4(∗) with the exception of compound 15 (agonist), and reduced or no effect at α7 and muscle subtypes.

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