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
Complete inhibition of fetal movement in the day 40 pregnant goat model by the piperidine alkaloid anabasine but not related alkaloids.
Benedict T. Green,S.T. Lee,John W. Keele,Kevin D. Welch,Daniel Cook,J. A. Pfister,William R. Kem +6 more
TL;DR: The results suggest that while experiments with TE‐671 cells provide valuable information and predictions of the actions of plant alkaloids on fetal movement, in vivo experiments are still required in order to determine the ability of an alkaloid to inhibit fetal movement in livestock species.
Book ChapterDOI
Cycloaddition reactions involving heterocyclic compounds as synthons in the preparation of valuable organic compounds. An effective combination of a computational study and synthetic applications of heterocycle transformations
Abstract: Publisher Summary By using computational tools, the chemical reactions can be aided in accomplishing transformation of the heterocycle into a valuable starting material in so far as its reactivity and selectivity toward certain chemical transformations are concerned. Utilizing semiempirical, ab initio, and density functional theory (DFT) methods, the chapter aims to demonstrate that this approach could be an integral part of complicated synthetic pathways for the preparation of chemicals. The chapter discusses this combinatory approach—namely, the incorporation of heterocyclic aromatic compounds as synthons into preparative synthetic schemes. The synthetic schemes used reflect the influence of computational results in the planning of the preparations of organic compounds performed in laboratories. They are used to demonstrate the validity of the computational (theoretical) and traditional synthetic chemistry to prepare an organic compound. The chapter discusses computational methodology, Diels–Alder reactions with five-membered heterocycles with one heteroatom—furan, pyrrole, and thiophene as dienophiles in reaction with acetylene, ethylene, and cyclopentadiene, addition of benzyne to furan, pyrrole, and thiophene, cycloaddition reactions with pyrrole as a diene for Diels–Alder reaction, Diels–Alder reactions with benzo[b] and benzo[c]-fused heterocycles. There are Diels–Alder reactions with five-membered heterocycles with two heteroatoms—addition of acetylene, ethylene, and cyclopropene to heterocycles with heteroatoms in the 1 and 2 positions, and the 1 and 3 positions. There are Diels–Alder reactions with five-membered heterocycles with three heteroatoms—addition of acetylene, ethylene, and cyclopropene to heterocycles with heteroatoms in 1, 2, and 3 positions and in the 1, 2, and 4 positions, addition of cyclopropene to heterocycles with heteroatoms in the 1, 2, and 5 positions. There is also investigation of the role of 1, 3, 4-oxadiazole as a diene in Diels–Alder reactions. There is detailed description of the cycloaddition reactions with activated heterocycles that have two or three heteroatoms.
Journal ArticleDOI
The enantiomers of epiboxidine and of two related analogs: Synthesis and estimation of their binding affinity at α4β2 and α7 neuronal nicotinic acetylcholine receptors
Clelia Dallanoce,Carlo Matera,Marco De Amici,Luca Rizzi,Luca Pucci,Cecilia Gotti,Francesco Clementi,Carlo De Micheli +7 more
TL;DR: The pharmacological analysis carried out on the three new enantiomeric pairs evidenced an overall negligible degree of enantioselectivity at both nAChRs subtypes, a result similar to that reported for both natural and unnatural epibatidine enantiomers at the same investigated receptor subtypes.
Journal ArticleDOI
Synthesis of Spirocyclic and Tricyclic Isoxazoline via 1,3‐Dipolar Cycloaddition Reactions
Melek Gul,Ahmet Tutar +1 more
TL;DR: The cycloadditions of the bicyclic monoterpenes (S)-(−)-camphene (1), (R)-(+)-a-pinene (2) with aryl and hetero-aryl nitrile oxides afforded new spirocyclic and tricyclic isoxazoline derivatives 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 whose biological activities were evaluated in bioassay studies.
Journal ArticleDOI
Regioselective Reduction of β‐Enaminoesters
Syed R. Hussaini,Mark G. Moloney +1 more
TL;DR: In this article, the regioselective reduction of β-enaminoesters derived from pyroglutamic acid can be readily achieved under mild conditions, and the reduction is shown to be reversible.