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NMR-Assisted Structure Elucidation of an Anticancer Steroid-β-Enaminone Derivative

Laboratory of Medicinal Chemistry, Endocrinology and Nephrology Unit, CHU de Québec—Research Center, Québec, QC G1V 4G2, Canada
Department of Molecular Medicine, Faculty of Medicine, Université Laval, Québec, QC G1V 0A6, Canada
Author to whom correspondence should be addressed.
Magnetochemistry 2017, 3(4), 37;
Received: 31 October 2017 / Revised: 15 November 2017 / Accepted: 17 November 2017 / Published: 21 November 2017
(This article belongs to the Special Issue Nuclear Magnetic Resonance Spectroscopy)
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The fortuitous modification of a quinoline-proline-piperazine side chain linked to a steroid in the presence of lithium (trimethylsilyl) acetylide has generated an unknown product that is more active than its precursor. After having characterized two β-enaminones (two-carbon homologation compounds) that were generated from a simplified model side chain, we have identified the unknown product as being the β-enaminone steroid derivative 1. NMR analysis, especially two-dimensional (2D) experiments (correlation spectroscopy (COSY), NOE spectroscopy (NOESY), heteronuclear single-quantum correlation (HSQC) and heteronuclear multiple-bond correlation (HMBC)) provided crucial information that was found essential in the characterization of enaminone 1. We also proposed a mechanism to rationalize the formation of this biologically active compound. View Full-Text
Keywords: enaminone; steroid; NMR; ethynylation; rearrangement; anti-cancer agent enaminone; steroid; NMR; ethynylation; rearrangement; anti-cancer agent

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Poirier, D.; Maltais, R. NMR-Assisted Structure Elucidation of an Anticancer Steroid-β-Enaminone Derivative. Magnetochemistry 2017, 3, 37.

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