MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE

Please use this identifier to cite or link to this item: http://hdl.handle.net/1811/55613

Show full item record

Files Size Format View
abstract.gif 75.92Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
PatriciaEcijaOhio.ppt 4.189Mb Microsoft PowerPoint View/Open
Slide1.GIF 116.9Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide2.GIF 46.77Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide3.GIF 35.23Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide4.GIF 23.00Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide5.GIF 25.63Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide6.GIF 21.39Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide7.GIF 31.01Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide8.GIF 29.43Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide9.GIF 73.72Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide10.GIF 7.247Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide11.GIF 190.5Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide12.GIF 61.89Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide13.GIF 27.15Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide14.GIF 73.21Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide15.GIF 49.22Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Slide16.GIF 106.4Kb GIF image Thumbnail of MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE

Title: MW SYSTEMATIC STUDY OF ALKALOIDS: THE DISTORTED TROPANE OF SCOPOLINE
Creators: Ecija, Patricia; Cocinero, Emilio J.; Basterretxea, Francisco J.; Fernandez, Jose A.; Castano, Fernando; Lesarri, Alberto
Issue Date: 2013
Publisher: Ohio State University
Abstract: Tropane alkaloids have diverse pharmacological uses and are well-known for their neurostimulant activity. Previous structure-activity-relationship established correlations between bioactivity and several aspects of ligand conformation and stereochemistry, including delicate intramolecular effects like nitrogen inversion$^{a}$. We have initiated a series of structural studies on tropane alkaloids$^{b}$, aimed to discerning their intrinsic stereochemical properties using rotational spectroscopy in supersonic jets$^{c}$. Here we extend these studies to the epoxytropanes, initially motivated to interrogate the influence of the epoxy group on nitrogen inversion and ring conformation. The rotational spectrum evidences a single structure in the gas phase, providing a first description of the (three ring) structurally-distorted tropane in scopoline. The determined rotational parameters of scopoline reveal the structural consequences of the intramolecular cyclation of scopine, which breaks the original epoxy group and creates a new ether bridge and a 7$\beta$-hydroxytropane configuration. The hydroxyl group further stabilizes the molecule by an $O-H \cdots N$ intramolecular hydrogen bond, which, in turn, forces the N-methyl group to the less stable axial form$^{b}$. The experimental work was supported by ab initio and DFT calculations.\\ $^{a}$ i) S.Singh, \emph{Chem. Rev.} 100, 925 (2000); ii) A. Krunic, D. Pan, W.J. Dunn III, S.V.S. Miariappan, \emph{Bioorg. & Med. Chem.} 17, 811 (2009).\\ $^{b}$ E.J. Cocinero, A. Lesarri, P. Ecija, J.-U. Grabow, J.A. Fernandez, F. Casta\~{n}o, \emph{Phys. Chem. Chem. Phys.} 12, 6076 (2010).\\ $^{c}$ E.J. Cocinero, A. Lesarri, P. Ecija, J.-U. Grabow, J.A. Fernandez, F. Casta\~{n}o, \emph{Phys. Chem. Chem. Phys.} 12, 12486 (2010).
Description: Author Institution: Departamento de Quimica Fisica, Facultad de Ciencia y Tecnologia, Universidad del Pais Vasco (UPV/EHU), Ap.644, E-48940, Bilbao, Spain; Departamento de Quimica Fisica y Quimica Inorganica, Facultad de Ciencias, Universidad de Valladolid, E-47011 Spain
URI: http://hdl.handle.net/1811/55613
Other Identifiers: 2013-MH-03
Bookmark and Share