A Spectroscopic Study of Colchicine in the Solid State and in Solution by Multinuclear Magnetic Resonance and Vibrational Circular Dichroism

Although almost 200‐years‐old, several unknown aspects remain to be explored of colchicine, the unique available drug for acute flares of gout. In this article, we report density‐functional theory (DFT) studies of geometry, energy, and NMR; 1H‐, 13C‐, and 15N‐NMR chemical shifts and some spin‐spin c...

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Bibliographic Details
Published in:Helvetica chimica acta 2014-04, Vol.97 (4), p.471-490
Main Authors: Virgili, Albert, Quesada-Moreno, Ma Mar, Avilés-Moreno, Juan Ramón, López-González, Juan Jesús, Ángeles García, M., Claramunt, Rosa M., Torres, M. Rosario, Jimeno, M. Luisa, Reviriego, Felipe, Alkorta, Ibon, Elguero, José
Format: Article
Language:English
Subjects:
Chiral solvating agents
Colchicine
NMR
Nuclear magnetic resonance
Racemization
Vibrational circular dichroism (VCD)
X-Ray crystallography
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Summary:Although almost 200‐years‐old, several unknown aspects remain to be explored of colchicine, the unique available drug for acute flares of gout. In this article, we report density‐functional theory (DFT) studies of geometry, energy, and NMR; 1H‐, 13C‐, and 15N‐NMR chemical shifts and some spin‐spin coupling constants, including the complete analysis of the saturated part (ring B); the assignment of both enantiomers by NMR using a chiral solvating agent; solid‐state NMR experiments of the different forms of natural and racemic colchicine, and IR and vibrational circular dichroism (VCD) studies of these same forms.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201300395