Oxysterols and hedgehog signaling
a technology of oxysterols and hedgehogs, applied in the field of oxysterols and hedgehog signaling, can solve the problems of difficult regulation and in particular inhibition of hedgehog signaling, and achieve the effect of inhibiting tumorigenesis
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example 1
of (E)-3-(4-fluorophenyl)-1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)prop-2-en-1-one (1)
[0336]
[0337]To a solution of pregnenolone (0.945 g, 3 mmol) and 4-fluorobenzaldehyde (0.446 g, 1.2 eq) in ethanol (30 mL) was added 2 mL of 4M KOH solution. After stirring for 24 at r.t., the resulting suspension was diluted with water (30 mL) and the solid product isolated by filtration, washed with water and dried by aspiration to give the title compound 1 (1.18 g, 93%).
example 2
of 3-(4-fluorophenyl)-1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)propan-1-one (2)
[0338]
[0339]To a suspension of 1 (0.25 g, 0.6 mmol) in hexane (2 mL) was added just enough EtOAc to dissolve the sample (5 mL). To the resulting solution, Pd / C catalyst (10% on carbon, 25 mg) was added and the mixture degassed via house vacuum. The mixture was then exposed to hydrogen gas (1 atm, balloon) for 30 min, after which TLC analysis revealed disappearance of starting material. The catalyst was removed by filtration over celite. After evaporation of the solvent, the title compound 2 was obtained and used without further purification. 1H NMR (CDCl3, 400 MHZ) δ 7.17-7.10 (2H, m), 6.95 (2H, dd, J=8.8, 8.8 Hz), 5.35-5.34 (1H, m), 3.48 (1H, dddd, J=10.9, 10.9, 5.5, 5.5 Hz), 2.83-2.80 (2H, m), 2.73-2.80 (2H, m), 2.53 (1H, dd, J=8.8, 8.8 Hz), 2.27-1.17 (15H, m), 1.06 (3H, s), 0.61 (3H, s). 13C NMR (CDCl3, 1...
example 3
of 3-(4-fluorophenyl)-1-((3S,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)propan-1-one (3)
[0340]
[0341]To a suspension of 1 (0.42 g, 1 mmol) in ethanol (10 mL) was added Pd / C catalyst (10% on carbon, 40 mg) and the mixture degassed via house vacuum. The mixture was then exposed to hydrogen gas (1 atm, balloon) for 72 h. The catalyst was removed by filtration over celite. The solvent was removed in vacuo to afford the title compound 3. 1H NMR (CDCl3, 400 MHZ) δ 7.17-7.10 (2H, m), 6.95 (2H, dd, J=8.8, 8.8 Hz), 3.52 (1H, dddd, J=10.9, 10.9, 5.5, 5.5 Hz), 2.83-2.80 (2H, m), 2.73-2.80 (2H, m), 2.53 (1H, dd, J=8.8, 8.8 Hz), 2.27-0.89 (15H, m), 0.75 (3H, s), 0.61 (3H, s). 13C NMR (CDCl3, 100 MHZ) δ 201.4, 161.2 (d, J=242 Hz), 137.1 (d, J=3.1), 129.6 (d, J=20 Hz), 115.1 (d, J=20 Hz), 71.3, 63.2, 56.8, 54.2, 46.0, 44.8, 44.6, 39.2, 38.15, 37.0, 35.5, 35.5, 32.0, 31.5, 28.9, 28.6, 24.4, 22.9, 21.2, 13.6, 12.3.
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