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Flavonol sulfonates derivatives and method for synthesizing same

A technology of flavonol sulfonate and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of low bioavailability, poor absorption, slow effect and the like, and achieve the effects of high bioavailability, improved solubility and good solubility

Inactive Publication Date: 2008-08-27
JIUJIANG UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a flavonol sulfonate derivative and its synthesis method, improve the physiological activity of quercetin compounds, improve their solubility, and solve the problems of low bioavailability and poor absorption in clinical application. , slow effect and low activity

Method used

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  • Flavonol sulfonates derivatives and method for synthesizing same
  • Flavonol sulfonates derivatives and method for synthesizing same
  • Flavonol sulfonates derivatives and method for synthesizing same

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Embodiment 1

[0045] The synthesis of embodiment 1 compound 6

[0046] 7-Benzenesulfonyloxy-3,5,3',4'-tetrabenzylquercetin

[0047] Synthesis of intermediate 7-hydroxy-3,5,3',4'-tetrabenzylquercetin 11,12. Take quercetin (0.4mmol, 0.1208g) and disperse it in 10mL of dichloromethane, add 0.2024g of benzyl chloride, and store at -10°C under the protection of Ar. Incubate for 0.5-24 hours. Filter the mixture, spin the filtrate to dryness under reduced pressure, and purify by column chromatography (chloroform / petroleum ether=10:1) to obtain pure tetrabenzylquercetin 11 and tribenzylquercetin 12. Intermediate 11: m.p.

[0048] 140-142°C (literature value: 140-142°C); intermediate 12: m.p.151-153°C (literature value: 150-152°C).

[0049] Synthesis of 7-benzenesulfonyloxy-3,5,3',4'-tetrabenzylquercetin 6. Take 11 (0.4mmol, 0.2648g) and disperse it in 10mL of dichloromethane, add 0.05g of benzenesulfonyl chloride, and store at -20°C under the protection of Ar. Incubate for 0.5-48 hours. Filter...

Embodiment 2

[0051] The synthesis of embodiment 2 compound 3

[0052] 7-Benzenesulfonyloxyquercetin

[0053] Synthesis of 7-Benzenesulfonyloxyquercetin 3. Take 6 (0.4mmol, 0.3208g) and add 10-20% reactant weight Pd / C (10%) and 60-90mL tetrahydrofuran-absolute ethanol (2:1-1:1), and replace the air with hydrogen repeatedly three times Then, stir with hydrogen at room temperature for 24-48 hours. The catalyst was removed by filtration, washed twice with THF, the solvent was distilled off under reduced pressure, and dried in vacuo to obtain a yellow solid.

[0054] 1 H NMR (400MHz, CDCl 3 ): δ6.23(J=1.8Hz, 1H, H6); 6.51(d, J=1.8Hz, 1H, H8), 7.06(d, J=8.8Hz, 1HH5'), 7.32(t, 1H, J =7.6Hz Phenylsulfonyl-4-H), 7.54(t, 2H, J=7.6Hz Phenylsulfonyl-3, 5-H), 7.87-7.95(m, 2H, H2', H6'), 8.11(d, 2H, J=7.8Hz, Phenylsulfonyl-2, 6-H), 9.56(s, 1H, OH), 10.41(s, 1H, OH), 10.74(brs, 1H, OH), 13.40(s, 1H, OH). m / z(EI)803.31(M + +1, 100%).

Embodiment 3

[0055] The synthesis of embodiment 3 compound 7

[0056] 4’,7-Diphenylsulfonyloxy-3,5,3’-tribenzylquercetin

[0057] Take 12 (0.4mmol, 0.2288g) and disperse it in 10mL of dichloromethane, add 0.05g of benzenesulfonyl chloride, and store at -20°C under the protection of Ar. Incubate for 0.5-48 hours. Filter the mixture, spin the filtrate to dryness under reduced pressure, and purify by column chromatography (chloroform / petroleum ether=20:1) to obtain a pure product.

[0058] 1 H NMR (400MHz, CDCl 3 ): δ4.99 (s, 2H, OCH 2 Ph), 5.12(s, 2H, OCH 2 Ph), 5.23(s, 2H, OCH 2 Ph), δ6.23(J=1.8Hz, 1H, H6); 6.51(d, J=1.8Hz, 1H, H8), 7.06(d, J=8.8Hz, 1H, H5'), 7.22-7.47( m, 17H, aromatic H), 7.54 (t, 4H, J = 7.6Hz Phenylsulfonyl-3, 5-H), 7.87-7.95 (m, 2H, H2', H6'), 8.11 (d, 4H, J = 7.8Hz, Phenylsulfonyl-2,6-H).m / z(EI)853.07(M + +1, 100%).

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Abstract

The invention relates to a flavonol sulfonic ester derivative and a relative synthesis method, wherein the formula of the flavonoid derivative is represented as right and provided with a flavonoid skeleton, R1, R2, R3, R4 and R5 are H, OH, aromatic sulfonic acid ester group and benzyloxy which can be same or different, the flavonol (quercetin or kaempferol) is reacted with aryl sulfonyl chloride selectively in the presence of organic alkali or inorganic alkali catalyst in organic solvent, or quercetin or kaempferol is selectively protected in organic solvent to be reacted with aryl sulfonyl chloride and de-protection. The invention has simple synthesis, mild reaction conditions and high yield. The invention improves the physiological activity of quercetin, improves relative solubility and resolves the defects in clinical application as low biological utilization, bad adsorption, low effect expression and low activity, and the product can be used as ester soluble anticancer agent, with strong inhibition on the growth of cancer cell and high biological utilization.

Description

Technical field [0001] The invention relates to a flavonol sulfonate derivative used as a prodrug and a synthesis method thereof. Background technique [0002] Quercetin (3, 5, 7, 3', 4'-pentahydroxyflavanone, 1) and kaempferol (5, 7, 3', 4'-terthydroxyflavanone, 2) are a kind of Or bioflavonoids with a wide range of physiological activities in medicinal plants. Quercetin and kaempferol have anti-tumor, anti-platelet, and antioxidant effects, and affect the activities of various enzymes (Ranelettl Fo. et al., Int. J. Cancer, 1992, 50 (3): 486). But Due to the poor water solubility and oil solubility of quercetin and kaempferol, the difficulty of absorption greatly limits their bioavailability and in vivo administration routes. Focusing on how to develop them into health food or clinical medicine, domestic and foreign scholars have done a lot of research work on quercetin and kaempferol in recent years. However, there are no examples of relatively successful transformation...

Claims

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Application Information

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IPC IPC(8): C07D311/30C07D311/22
Inventor 彭游
Owner JIUJIANG UNIVERSITY
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