Epibatidine isomers and analogues: Structure–activity relationships

https://doi.org/10.1016/j.bmcl.2006.08.049Get rights and content

Abstract

Binding affinities for a range of epibatidine isomers and analogues at the α4β2 and α3β4 nAChR subtypes are reported; compounds having similar N–N distances to epibatidine show similar, high potencies.

References and notes (15)

  • A.L. Cashin et al.

    J. Am. Chem. Soc.

    (2005)
    R.A. Glennon et al.

    Bioorg. Med. Chem. Lett.

    (2004)
    S.B. Hansen et al.

    EMBO J.

    (2005)
  • C.D. Cox et al.

    J. Chem. Soc., Perkin Trans. 1

    (2001)
    D.M. Hodgson et al.

    J. Chem. Soc., Perkin Trans. 1

    (2001)
  • D.L. Bai et al.

    J. Org. Chem.

    (1996)
  • R.W. Fitch et al.

    Bioorg. Med. Chem.

    (2004)
  • J. Zhou et al.

    J. Am. Chem. Soc.

    (2004)
  • T.F. Spande et al.

    J. Am. Chem. Soc.

    (1992)
  • A.A. Jensen et al.

    J. Med. Chem.

    (2005)
    F.I. Carroll

    Bioorg. Med. Chem. Lett.

    (2004)
    F.I. Carroll et al.

    J. Med. Chem.

    (2002)
    W.H. Bunnelle et al.

    Curr. Top. Med. Chem.

    (2004)
There are more references available in the full text version of this article.

Cited by (16)

  • Chemoenzymatic enantioselective synthesis of 7-azabicyclo[2.2.1]heptane derivatives

    2011, Tetrahedron Asymmetry
    Citation Excerpt :

    This natural product is a powerful non-opioid analgesic (several hundred times more potent than morphine), and shows a high affinity for neuronal nicotinic acetylcholine receptors.2,3 7-Azabicyclo[2.2.1]heptane-based compounds have found many applications in medicinal chemistry,4–11 organic synthesis,12–15 peptide chemistry,16–21 and material science.22 Furthermore, these N-bridged bicycles exhibit interesting physical properties: the corresponding amides are not planar but distorted due to nitrogen pyramidalization23 whereas the corresponding tertiary amines have exceptionally high nitrogen inversion barriers (bicyclic effect).24,25

  • Smoking, nicotine and neuropsychiatric disorders

    2010, Neuroscience and Biobehavioral Reviews
View all citing articles on Scopus
View full text