Journal ArticleDOI
Epibatidine: a novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an ecuadoran poison frog
Thomas F. Spande,H. M. Garraffo,M. W. Edwards,Herman J. C. Yeh,Lewis K. Pannell,John W. Daly +5 more
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TLDR
A potent non-opioid analgesic, epibatidine, has been isolated from skins of the Ecuadoran poison frog, Epipedobates tricolor, and its structure determined by MS, IR, and 1 H NMR analyses as exo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane represents a unique new class of alkaloids.Abstract:
A potent non-opioid analgesic, epibatidine, has been isolated from skins of the Ecuadoran poison frog, Epipedobates tricolor, and its structure determined by MS, IR, and 1 H NMR analyses as exo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane. It represents a unique new class of alkaloidsread more
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Application of an organozinc reagent derived from (S)-pyroglutamic acid: a formal synthesis of epibatidine
Willem F. J. Karstens,M. J. Moolenaar,Floris P. J. T. Rutjes,Urszula Grabowska,W. Nico Speckamp,Henk Hiemstra +5 more
TL;DR: In this article, a formal total synthesis of natural (−)-epibatidine has been developed, which is a copper-I-mediated coupling of an (S)-pyroglutamic acid-derived organozinc reagent with 1-iodo-3-trimethylsilyl-1-propyne and an N-acyl- or N-sulfonyliminium ion cyclization.
Journal ArticleDOI
Neuronal nicotinic acetylcholine receptors as drug targets.
Mark J Suto,Niki Zacharias +1 more
TL;DR: In vitro and in vivo data, homology modelling, and the identification of small-molecule agonists, have confirmed nAChRs as valid drug discovery targets and several compounds are now in clinical development for the treatment of pain, smoking cessation and cognitive disorders.
Journal ArticleDOI
Nitrogen bridge homoepibatidines. syn-6- and syn-5(6-chloro-3-pyridyl)isoquinuclidines
Grant R. Krow,Osbert H. Cheung,Zilun Hu,Qiuli Huang,John Hutchinson,Nian Liu,Kevin T. Nguyen,Scott Ulrich,Jing Yuan,Yushi Xiao,Donna M. Wypij,Fangming Zuo,Patrick J. Carroll +12 more
TL;DR: The N-bridge vicinal and distal 6-(6-Cl-3-pyridyl)-2-azabicyclo[2.2]octane homologs of the potent nicotinic receptor agonist epibatidine have been synthesized.
Journal ArticleDOI
The effect of DMSO on the borohydride reduction of a cyclohexanone: A formal enantioselective synthesis of (+)-epibatidine
TL;DR: In this paper, an asymmetric synthesis of (+)-epibatidine is described which uses the increased stereoselectivity of a borohydride reduction induced by the presence of DMSO.
Journal ArticleDOI
5-Azidoepibatidine: an exceptionally potent photoaffinity ligand for neuronal α4β2 and α7 nicotinic acetylcholine receptors
TL;DR: Racemic 5-azidoepib atidine was synthesized via 5-aminoepibatidine as a candidate photoaffinity ligand with exceptionally high affinity at the mammalian neuronal nicotinic receptors and excellent photoreactivity.