Benzobinaphthoquinone derivative with anticancer activity
A technology of benzodinaphthoquinone and anti-cancer activity, which is applied in the direction of sugar derivatives, organic active ingredients, and medical preparations containing active ingredients, etc., can solve the problems of research on the activity of chemical ingredients, and achieve strong anti-tumor activity and low toxic effect
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Embodiment 1
[0025] Preparation of p-hydroxymethoxybenzobisjulquinone:
[0026]Soak 100 kg of early spring fresh young leaves of Juglans mandshurica with 400 kg of 95% ethanol for 48 hours, concentrate the ethanol soaking solution to extract, disperse with water, and then extract with petroleum ether, chloroform, and ethyl acetate in sequence. Concentrate the ethyl acetate phase, use the dry loading method, pass through the silica gel chromatography column, and use the chloroform-methanol gradient elution, collect the eluate eluted with chloroform:methanol=4:1, and concentrate the eluate , through a sephadex LH-20 chromatographic column, eluted with methanol, and the red component was collected. The red fraction was passed through a silica gel H decompression column, using chloroform:methanol=4:1 as the eluent, the pressure was 0.02MP, and the eluate with an Rf value of 0.45 was collected. The eluent is further purified by high-performance liquid chromatography. The stationary phase of hi...
Embodiment 2
[0048] Preparation of 1"-methoxy-5,5',2"-acetoxy-benzodinaphthoquinone:
[0049] 100 mg of the product of the above example was dissolved in 10 ml of pyridine, 500 mg of acetic anhydride was added thereto, and after stirring for 4 hours, 96 mg of the target product was obtained as a red crystalline solid. m.p.>300°C. Mass spectra and various spectroscopic data indicated that the product was the acetate ester of Compound 1 of Example above.
[0050] Molecular formula is C 29 h 18 o 11 High resolution mass spectrometry M + =542.0431
[0051] IR (KBr) 2934, 2912, 1781, 1711, 1641, 1590, 1483, 745, 710,
[0052] 1 H NMR (DMSO-d6) δ, ppm: 2.08 (s,, 9H, CH 3 )3.01 (s, 3H, OCH 3 ), 7.16~7.60 (m, 6H, aromatic H).
[0053] 13 CNMR (DMSO-d6):
[0054] carbon ppm
[0055] 1,1' 182.20
[0056] 2,2' 124.30
[0057] 3,3' 132.68
[0058] 4,4' 182.89
[0059] 5,5' 153.80
[0060] 6,6' 125.13
[0061] 7,7' 132.61
[0062] 8,8' 126.25
[0063] 9,9' 134.70
[0064] 10, 10'...
Embodiment 3
[0071] Preparation of double juglquino 1''-methoxy-benzene-2''-O-glucopyranoside:
[0072] Weigh 1.2g of sodium hydroxide and 0.1g of potassium iodide and dissolve them in 20ml of water, then weigh 0.2g of the product in Example 1, and add them to the above alkali solution in batches under magnetic stirring to obtain a light red suspension, and then add 20mL of Acetone, the solution becomes clear and transparent. Weigh 2.63 g of α-bromoacetylglucose, dissolve it in 20 ml of acetone, and slowly drop it into the above-mentioned alkali solution through a constant pressure funnel. After reacting for 12 hours, TLC detects that (petroleum ether: ethyl acetate=3:2 ), the reaction was complete, the acetone was evaporated by distillation under reduced pressure, the residue was poured into the ice-water mixture, fully stirred, a solid was precipitated, filtered by suction, the obtained solid was crushed and washed 2-3 times with saturated sodium carbonate solution, and then washed with ...
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