Anthraquinone compounds and applications thereof
A compound, anthraquinone technology, applied in the field of simulating BH3-only proteins, can solve the problems of insufficient BH3 similarity, large toxic side effects, and toxic side effects
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Embodiment 1
[0046] Example 1: Preparation of 6-bromo-2,3-dihydroxyanthraquinone-9,10-dione
[0047]
[0048] Take 4.44g (0.03mol) of phthalic anhydride, add 20ml of water, 2.4g (0.06mol) of NaOH, stir at room temperature until completely dissolved. After cooling, add 3ml of liquid bromine dropwise, and react at 90°C. If there is solid precipitation in the middle, add an appropriate amount of water. After 6 hours of reaction of the clear solution, the color changed from dark red to light, and solids precipitated out after cooling overnight. Filter the solid, discard the filtrate, dissolve the solid in 20ml of hot water, add HCl to neutralize to pH<4, and extract with ethyl acetate. After extraction three times, the organic layer was dried over anhydrous magnesium sulfate for 2 hours, filtered, and the filtrate was spin-dried to obtain 1.86 g of 4-bromo-phthalic acid as a white solid with a yield of 66.9% and a melting point of 164°C.
[0049] Weigh 0.735 g of dry 4-bromo-phthalic acid...
Embodiment 2
[0052] Example 2: Preparation of 6-bromo-1,2,3-trihydroxyanthraquinone-9,10-dione
[0053] Take 4.44g (0.03mol) of phthalic anhydride, add 20ml of water, 2.4g (0.06mol) of NaOH, stir at room temperature until completely dissolved. After cooling, add 3ml of liquid bromine dropwise, and react at 90°C. If there is solid precipitation in the middle, add an appropriate amount of water. After 6 hours of reaction of the clear solution, the color changed from dark red to light, and solids precipitated out after cooling overnight. Filter the solid, discard the filtrate, dissolve the solid in 20ml of hot water, add HCl to neutralize to pH<4, and extract with ethyl acetate. After extraction three times, the organic layer was dried over anhydrous magnesium sulfate for 2 hours, filtered, and the filtrate was spin-dried to obtain 1.86 g of 4-bromo-phthalic acid as a white solid with a yield of 66.9% and a melting point of 164°C.
[0054]
[0055] Weigh 0.735 g of dry 4-bromo-phthalic a...
Embodiment 3
[0058] Example 3: Preparation of 6-phenylthio-2,3-dihydroxyanthraquinone-9,10-dione
[0059]
[0060] Take 0.16g (0.5mmol) 6-bromo-2,3-dihydroxyanthraquinone-9,10-dione, 0.33g (3mmol, 310uL) thiophenol, 10mgCuI, add to 10mL DMF, N 2 Under protection, heat and stir at 140°C for 6h. After cooling, add 50 mL of 10% HCl solution by mass fraction, let stand for 1 hour, and filter. The solid was dried, dissolved in ethyl acetate, filtered, the filtrate was dried, and the solvent was evaporated to obtain a khaki crude product. Dry loading, ethyl acetate:petroleum ether=1:1 (1% acetic acid) was used as the eluent, and silica gel column separation gave 0.043 g of a yellow solid with a yield of 24.7%.
[0061] Structural characterization: M.p.251°C (sublimation). 1 H NMR(400M,DMSO):δ10.63(d,J=12Hz,2H),8.02(d,J=8.0Hz,1H),7.63(d,1H),7.52(m,J=12Hz,5H) ,7.45(s,1H), 7.37(d,J=8Hz,2H),TOF MS(EI + ):C 20 h 12 o 4 S, (m / z): calcd for 348.37, found 348.05.
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