NMR-Assisted Structure Elucidation of an Anticancer Steroid-β-Enaminone Derivative
| Autor: | René Maltais, Donald Poirier |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
anti-cancer agent
Trimethylsilyl Stereochemistry medicine.medical_treatment rearrangement 01 natural sciences Steroid lcsh:Chemistry 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Materials Chemistry medicine Side chain enaminone steroid NMR ethynylation 010405 organic chemistry Acetylide 3. Good health 0104 chemical sciences Electronic Optical and Magnetic Materials chemistry Heteronuclear molecule lcsh:QD1-999 Chemistry (miscellaneous) 030220 oncology & carcinogenesis Two-dimensional nuclear magnetic resonance spectroscopy Derivative (chemistry) Heteronuclear single quantum coherence spectroscopy |
| Zdroj: | Magnetochemistry; Volume 3; Issue 4; Pages: 37 Magnetochemistry, Vol 3, Iss 4, p 37 (2017) |
| ISSN: | 2312-7481 |
| DOI: | 10.3390/magnetochemistry3040037 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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