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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Unique spirocyclopiperazinium salt I: synthesis and structure-activity relationship of spirocyclopiperazinium salts as analgesics.
TL;DR: Based on the structure of compound 3, two series of spirocyclopiperazinium derivatives 7a-n and 10a-h were synthesized and evaluated for their in vivo analgesic and sedative activities as mentioned in this paper.
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Regioselective rearrangement of 7-azabicyclo[2.2.1]hept-2-aminyl radicals: first synthesis of 2,8-diazabicyclo[3.2.1]oct-2-enes and their conversion into 5-(2-aminoethyl)-2,3,4-trihydroxypyrrolidines, new inhibitors of α-mannosidases
TL;DR: In this paper, the enantiomerically pure 2,8-diazabicyclo[3.2.1]oct-2-ene derivatives (+)-5 and (-)-5 have been obtained from 2-azido-3-tosyl-7-azabicyclecyclo[2.2]heptanes and their enantiomers, by ring expansion under radical conditions, by transforming them into hemiaminals 9 ((3S,4R,5R)- and 10 ((3R,4S,5S)-5-(
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Synthesis and structure–activity relationship of novel pyridyl ethers for the nicotinic acetylcholine receptor
TL;DR: The preparation of novel pyridyl ethers as ligands for the nicotinic acetylcholine receptor (nAChR) is described and Variations of the ring size of the azacycle and substitution on the pyridine had dramatic effects on receptor binding affinity with IC50s at the alpha4beta2 nA ChR.
Journal ArticleDOI
Synthesewettlauf zum Epibatidin, einem neuartigen Naturstoff mit hoher analgetischer Wirkung
TL;DR: The Epibatidine Competition: Synthetic Work on a Novel Natural Analgetic======\/\/\/\/\/\/£££€££/$££ £££$££ $£ £/$£ £ ££ £€£ £$£ £20/$£20 ££20/$20/$30/$30 £20 £10 independent syntheses were published in 1993/1994 as mentioned in this paper demonstrating the interaction of classical and modern synthetic methods.