Palladium catalyzed synthesis of benzannulated steroid spiroketals.
Martha C Mayorquín-TorresJuan Carlos González-OrozcoMarcos Flores-ÁlamoIgnacio Camacho-ArroyoMartin A Iglesias-ArteagaPublished in: Organic & biomolecular chemistry (2020)
Nine cytotoxic [5/7] and [6/6] benzannulated steroid spiroketals were synthesized by palladium catalyzed spiroketalization of 5α and 5β-alkynediols derived from testosterone, diosgenin and cholesterol. The regioselectivity of the spiroketalization reaction is decisively influenced by the α or β-orientation of the hydroxyl group at C-5. NMR and single crystal X-ray diffraction corroborated the structure of the obtained compounds. Compounds bearing a cholestane skeleton exhibited higher cytotoxicity against U251 and T47D cells, and the BrdU incorporation assay suggests that the synthesized spiroketals inhibit cell proliferation.
Keyphrases
- cell proliferation
- high resolution
- induced apoptosis
- cell cycle arrest
- magnetic resonance
- solid state
- high throughput
- electron microscopy
- cell cycle
- replacement therapy
- endoplasmic reticulum stress
- cell death
- signaling pathway
- low density lipoprotein
- mass spectrometry
- dual energy
- oxidative stress
- computed tomography
- crystal structure