NMR-Assisted Structure Elucidation of an Anticancer Steroid-β-Enaminone Derivative
AbstractThe 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
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Poirier, D.; Maltais, R. NMR-Assisted Structure Elucidation of an Anticancer Steroid-β-Enaminone Derivative. Magnetochemistry 2017, 3, 37.
Poirier D, Maltais R. NMR-Assisted Structure Elucidation of an Anticancer Steroid-β-Enaminone Derivative. Magnetochemistry. 2017; 3(4):37.Chicago/Turabian Style
Poirier, Donald; Maltais, René. 2017. "NMR-Assisted Structure Elucidation of an Anticancer Steroid-β-Enaminone Derivative." Magnetochemistry 3, no. 4: 37.
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