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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Approaches to syn-7-substituted 2-azanorbornanes as potential nicotinic agonists; synthesis of syn- and anti-isoepibatidine.
TL;DR: In this article, the first syn-7-hydroxy-2-azabicyclo[2.2.1]heptane derivative was proposed, based on the N-protecting group.
Journal ArticleDOI
An efficient route to 6-(het)aryl-2-methyl-2,3-dihydro-1H-pyridin-4-ones as potential nAChRs ligands
TL;DR: A new efficient pathway to synthesise 6-(het)aryl-2-methyl-2,3-dihydro-1H-pyridin-4-ones is described.
Journal ArticleDOI
Synthesis of Epibatidine‐Related Δ2‐Isoxazoline Derivatives and Evaluation of Their Binding Affinity at Neuronal Nicotinic Acetylcholine Receptors
Clelia Dallanoce,Paola Bazza,Giovanni Grazioso,Marco De Amici,Cecilia Gotti,Loredana Riganti,Francesco Clementi,Carlo De Micheli +7 more
TL;DR: In this paper, a 1,3-dipolar cycloaddition-based strategy was used to synthesize Δ2-isoxazoline derivatives for α4β2 and α7 neuronal acetylcholine receptor (nAChR) subtypes.
Journal ArticleDOI
Nickel–Copper-Catalyzed C(sp2)N Cross-Coupling of Cyclic and Bridged Amides: An Access to Cyclic Enamides and Alkenyl Vince Lactams
TL;DR: An efficient C(sp2)N cross-coupling of styrenyl and vinyl halides with cyclic and bridged amides catalyzed by nickel acetonylacetonate [Ni(acac)2] and copper(I) iodide (CuI) in the absence of any ligand has been developed as mentioned in this paper.
Journal ArticleDOI
Structure–Activity Studies of 7-Heteroaryl-3-azabicyclo[3.3.1]non-6-enes: A Novel Class of Highly Potent Nicotinic Receptor Ligands
Scott R. Breining,Melvin Matt S,Bhatti Balwinder Singh,Gary D. Byrd,Melanie N. Kiser,Christopher D. Hepler,Dawn N. Hooker,Jenny Z. Zhang,Leslie A Reynolds,Lisa R Benson,Fedorov Nikolai,Serguei S. Sidach,J. Pike Mitchener,Linda Lucero,Ronald J. Lukas,Paul Whiteaker,Daniel Yohannes +16 more
TL;DR: The structure-activity relationships (SAR) for a novel series of 7-heteroaryl-3-azabicyclo[3.3.1]non-6-enes are reported and many of the analogues for activity at multiple nicotinic subtypes are characterized.