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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Journal ArticleDOI
Synthesis of (−)-epibatidine
Wen-Hua Chiou,Yu-Min Chiang +1 more
TL;DR: An asymmetric synthesis to the dendrobatid alkaloid (−)-epibatidine has been described in this article, featuring chiral resolution of both optically pure 7-azabicyclo[2.2.1]heptanecarboxylic acid, and subsequent transformations to (−-epibaratidine.
Journal ArticleDOI
Mechanistic analysis of intramolecular free radical reactions toward synthesis of 7-azabicyclo[2.2.1]heptane derivatives.
TL;DR: The mechanism and the critical effect of the 7-nitrogen protecting group on the outcome of these radical-mediated cyclizations are discussed and theoretical findings account for unexpected experimental results and can assist in the selection of proper precursors for a successful cyclization.
Journal ArticleDOI
An Improved Practical Route to (±)‐Epibatidine through L‐Proline Catalyzed Intramolecular Michael Addition
TL;DR: In this article, the authors describe a rapid and practical synthetic route involving six-step reactions towards the diastereoselectively synthesis of (±)-endo-Epibatidine, starting from 6-chloro-3 pyridinecarboxaldehye.
Book ChapterDOI
Marine-derived nicotinic receptor antagonist toxins: Pinnatoxins and alpha conotoxins
TL;DR: The threat of these toxins to animal and human health, their pharmacological and toxicological characteristics, their use as tool compounds and the therapeutic potential of nicotinic toxins are discussed.
Journal ArticleDOI
Syntheses of (+/-)-homoepibatidine analogues.
Yonghyun Kim,Chang-Young Oh,Kee-Young Lee,Yiu-Suk Lee,Young Hoon Jung,Hyun-Ju Park,Won-Hun Ham +6 more
TL;DR: Syntheses of (±)-homoepibatidine analogues, which contain the 8-azabicyclo [3.2.1]octane ring system, were achieved by using palladium-catalyzed reductive-coupling reaction from and the analgesic activity was tested by Mouse writhing antinociceptive assay.