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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A practical enantioselective synthesis of epibatidine
TL;DR: Two different syntheses of Epibatidine (1) were designed and carried out using easily accessible reagents and convenient reaction conditions as mentioned in this paper, and the ring closure of the prochiral precursor 4 catalyzed by optically active α-phenyl-ethyl-amine gave the key intermediate 5 in over 80% ee from which the natural product (−)- 1 has been prepared.
Journal ArticleDOI
Formal synthesis of natural epibatidine and of its enantiomer: Use of radical cyclization in an enantiospecific route
TL;DR: In this paper, pyroglutamic acid was converted into the (phenylthio)acetylene 14, which undergoes radical cyclization to the 7-azabicyclo[2.2.1]heptane 15.
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New-generation radiotracers for nAChR and NET.
Yu-Shin Ding,Joanna S. Fowler +1 more
TL;DR: This article focuses on the development and translation of radiotracers for PET studies of the nicotinic acetylcholine receptor and the norepinephrine transporter, two molecular systems that urgently need such an important tool to better understand their functional significance in the living human brain.
Journal ArticleDOI
Synthesis and structure–Activity data of some new epibatidine analogues
TL;DR: The high-pressure Diels-Alder reaction of N-carbomethyoxypyrroles and phenyl vinyl sulfone affords versatile intermediates for the palladium-catalyzed preparation of new epibatidine analogues.
Journal ArticleDOI
Synthesis, receptor binding and QSAR studies on 6-substituted nicotine derivatives as cholinergic ligands
Malgorzata Dukat,Matthew Dowd,M. Imad Damaj,Billy R. Martin,Mohamed El-Zahabi,Richard A. Glennon +5 more
TL;DR: It would appear that lipophilic substituents at the pyridine 6-position contribute to nAChR affinity of nicotine analogs, but that affinity is further modulated by the steric size of this substituent in that increased size results in decreased affinity.