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Dyestuff lignin sulfonic acid ester derivatices and preparation method thereof

A technology for sulfonic acid esters and derivatives, applied in the field of genistein sulfonic acid ester derivatives and their preparation, can solve the problems of poor water solubility and fat solubility of genistein, unclear application prospects, successful anti-cancer transformation and the like

Inactive Publication Date: 2008-07-09
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the poor water solubility and fat solubility of genistein, the application prospect is not clear
At present, there are many kinds of derivatives reported at home and abroad, but there are no examples of successful transformation in anti-cancer

Method used

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  • Dyestuff lignin sulfonic acid ester derivatices and preparation method thereof
  • Dyestuff lignin sulfonic acid ester derivatices and preparation method thereof
  • Dyestuff lignin sulfonic acid ester derivatices and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Compound 4', the synthesis of 5-dihydroxyl-7-benzenesulfonyloxy isoflavone

[0035] Disperse genistein (0.4mmol, 0.108g) in 10mL of dichloromethane, add 0.01g of potassium tert-butoxide, and slowly add 0.48mmol (0.0847g) of benzenesulfonyl chloride dropwise at -20°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 / acetone=10:1) to obtain a pure product.

[0036] 1 H NMR (400MHz, CDCl 3 ): δ12.7 (1H, s, 5-OH), 7.94 (1H, s, 2-H), 7.90 (2H, d, J=7.7Hz, 2”, 6”-benH), 7.72 (1H, t, J=7.5Hz, 4"-H), 7.59 (2H, t, J=7.7Hz, 3", 5"-benH), 7.39 (2H, d, J=8.5Hz, 2', 6'- ArH), 6.90 (2H, d, J=8.5Hz, 3', 5'-ArH), 6.77 (1H, d, 4 J=2.0Hz, 8-ArH), 6.39 (1H, d, 4 J=2.0Hz, 6-ArH), 5.39 (1H, s, 4'-OH); m / z (EI) 411.08 (M + +1, 100%).

Embodiment 2

[0037] Example 2 Compound 5-dihydroxyl-4', the synthesis of 7-diphenylsulfonyloxy isoflavone

[0038] Genistein (0.4mmol, 0.108g) was dispersed in 10mL of dichloromethane, 0.01g of KOH was added, and 0.96mmol (0.1694g) of benzenesulfonyl chloride was slowly added dropwise at -20°C under the protection of Ar. Incubate for 0.5 to 24 hours. Filter the mixture, spin the filtrate to dryness under reduced pressure, and purify by column chromatography (chloroform / acetone=20:1) to obtain a pure product.

[0039] 1 H NMR (400MHz, CDCl 3 ): δ12.7 (1H, s, 5-OH), 7.95 (1H, s, 2-H), 7.90 (4H, d, J=8.7, 9.3Hz, 2", 6"-benH, 2, 6-benH), 7.72(2H, m, 4”-H, 4-H), 7.58(4H, t, m 3”, 5”-benH, 3, 5-H), 7.46(2H , d, J=8.5Hz, 2', 6'-ArH), 7.09 (2H, d, J=8.5Hz, 3', 5'-ArH), 6.77 (1H, d, 4 J=1.5Hz, 8-ArH), 6.39 (1H, d, 4 J=1.5Hz, 6-ArH); m / z (EI) 550.96 (M + +1, 100%).

Embodiment 3

[0040] Example 3 Compound 4', 5, the synthesis of 7-triphenylsulfonyloxy isoflavones

[0041] Genistein (0.4mmol, 0.108g) was dispersed in 10mL of dichloromethane, 0.01g of NaOH was added, and 1.44mmol (0.2541g) of benzenesulfonyl chloride was slowly added dropwise at -20°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 / acetone=50:1) to obtain a pure product.

[0042] 1 H NMR (400MHz, CDCl 3 ): δ7.98 (2H, d, J=7.6Hz, 2"", 6""-benH), 7.90 (4H, d, J=7.6Hz, 2", 6"-benH, 2, 6 -benH), 7.82 (1H, s, 2-H), 7.77 (1H, t, 4””-H), 7.72 (2H, t, 4”, 4-H), 7.58 (6H, m, 3 ", 3, 3"", 5", 5, 5""-benH), 7.39 (2H, d, J=8.5Hz, 2', 6'-ArH), 7.22 (1H, d, 4 J=1.88Hz, 8-ArH), 7.05 (2H, d, J=8.5Hz, 3', 5'-ArH), 6.81 (1H, d, 4 J=1.5Hz, 6-ArH); m / z (EI) 691.18 (M + +1, 100%).

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Abstract

A genistein sulfonates derivative and the preparation process are characterized in that the chemical general formula is showed, wherein R3 is toluene sulfonyl-oxygen, R1 is OR4, R2 is OR5, and R4 and R5 are hydrogen, methyl, ethyl group, benzene sulfonyl and acetyl.

Description

technical field [0001] The invention relates to a genistein sulfonate derivative and a preparation method thereof. Background technique [0002] Genistein (4',5,7-trihydroxyisoflavone) has a variety of physiological activities: anti-estrogen properties, can inhibit tyrosine kinase (an enzyme produced by an oncogene that can promote the growth of certain tumors) It can prevent the growth of cancer cells; inhibit the action of some other enzymes in the process of cancer development, promote the differentiation of cancer cells and transform them back into normal cells; inhibit capillary angiogenesis (angiogenisis). Is a powerful antioxidant that protects cells from free radical attack. In view of the above-mentioned multiple activities of genistein, it is very likely to be used to prevent or treat various cancers. (Li W, et al. Oncol. Res. 1998, 10, 117) Experimental evidence also shows that genistein can lower cholesterol, relieve menopausal syndrome, prevent and treat osteo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36A61P35/00
Inventor 彭游邓泽元
Owner NANCHANG UNIV
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