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Isoflavone sulfonate derivatives and synthetic method thereof

A technology of isoflavone sulfonate and synthesis method, which can be applied in the directions of drug combination, pharmaceutical formula, organic active ingredient, etc., can solve the problems of poor absorption, slow effect and low activity, etc.

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

In order to improve the anticancer activity of daidzein compounds, expand the anticancer spectrum, improve the solubility of daidzein, and solve the shortcomings of low bioavailability, poor absorption, slow effect and low activity in clinical application, daidzein It is of great significance to modify it and find more effective anticancer drugs.

Method used

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  • Isoflavone sulfonate derivatives and synthetic method thereof
  • Isoflavone sulfonate derivatives and synthetic method thereof
  • Isoflavone sulfonate derivatives and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 Synthesis of Compound 4'-Acetoxyl-7-Hydroxy Isoflavones

[0019] Synthesis of intermediate 4'-hydroxy-7-benzenesulfonyloxyisoflavone. Take daidzein (0.4mmol, 0.1016g) and disperse it 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.

[0020] 1 H NMR (400MHz, CDCl 3 ): δ 8.21 (1H, d, J = 8.8Hz), 7.97 (1H, s), 7.90 (2H, d, J = 7.6Hz,), 7.72 (1H, t, J = 8.0Hz,), 7.58 ( 2H, t, J=7.6, 8.0Hz,), 7.43 (2H, d, J=8.4Hz,), 6.98 (1H, d, 4 J = 2.0Hz), 6.90 (2H, d, J = 8.4Hz,), 6.86 (1H, dd, J = 2.0, 8.8Hz), , 5.00 (1H, s); m / z (EI) 395.12 (M + +1, 100%).

[0021] Synthesis of 4'-Acetoxy-7-Hydroxyisoflavones. Take the intermediate 4'-hydroxyl-7-benzenesulfony...

Embodiment 2

[0023] Example 2 Synthesis of compound 4'-methoxy-7-benzenesulfonyloxyisoflavone Method 1: Synthesis of 4'-methoxy-7-benzenesulfonyloxyisoflavone. Take 0.4mmol intermediate 4'-hydroxyl-7-benzenesulfonyloxy isoflavone 6 (0.1576g) and dissolve it in 10mL acetone, add 0.1g potassium carbonate, add 0.15mL dimethyl sulfate at room temperature, at 25 ℃~60℃ for 5 hours. The reaction mixture was filtered, the filtrate was spin-dried, and purified by column chromatography (chloroform / acetone=5:1) to obtain a pure product. Method 2: Synthesis of intermediate 4'-methoxy-7-hydroxyisoflavone. Take daidzein (0.4mmol, 0.1016g) and disperse it in 10mL of dimethylformamide, add 0.1g of potassium carbonate, add 0.15mL of dimethyl sulfate at room temperature, and react at 25°C to 60°C for 3h. The reaction solution was added to 20 mL of cold water, filtered, the filter cake was washed with water, and purified by column chromatography to collect the second band. White solid, 0.040g, yield 25%, ...

Embodiment 3

[0025] Example 3 Synthesis of Compound 4'-Ethoxy-7-Benzenesulfonyloxy Isoflavone

[0026] Method 1: Synthesis of 4'-ethoxy-7-benzenesulfonyloxy isoflavone, take 0.4mmol compound 6 (0.1576g) and dissolve it in 10mL acetone, add 0.1g potassium hydroxide and 0.2L water, in Slowly add 0.15mL diethyl sulfate at room temperature, and react at 25°C~60°C for 5h. The reaction mixture was filtered, the filtrate was spin-dried, and purified by column chromatography (chloroform / acetone=5:1) to obtain a pure product.

[0027] Method 2: Synthesis of intermediate 4'-ethoxy-7-hydroxyisoflavone. Take daidzein (0.4mmol, 0.1016g) and disperse it in 10mL dimethylformamide, add 0.1g potassium carbonate, 0.15 mL of diethyl sulfate was added under low temperature, and the reaction was carried out at 25° C. to 60° C. for 3 h. The reaction solution was added to 20 mL of cold water, filtered, the filter cake was washed with water, and purified by column chromatography to collect the first band. Whit...

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Abstract

An isoflavone sulfonates derivative and the synthesis process are characterized in that the chemical structural general formula is that R1 is OR3 and OCOR4, R2 is aromatic sulfonic acid ester group, and R3 and R4 is C1-C2 alkyl. The compound ester solubility of the invention is greatly improved compared with soybean aglycone.

Description

technical field [0001] The invention relates to an isoflavone sulfonate derivative, its synthesis method and its use as an anticancer drug. Background technique [0002] The isoflavone compound daidzein (Daidzein, 4', 7-dihydroxyisoflavone) has the physiological activity of inhibiting the growth of cancer cells (Sarhyyamoonhy N.Wang T.T.Y.1997.14: 2384). However, when daidzein is treated with HL-60 cells , the effect on cell growth induction and differentiation is weak, and the number of NBT positive cells is less than 10% (Jiao Lu, Chinese Journal of Hematology, 1990, 11, 83). Tablets or capsules made from it are mainly used to treat coronary heart disease, cerebral thrombosis, cerebral infarction, sequelae of cerebral hemorrhage, and can also be used for neck pain, headache, dizziness and early sudden deafness caused by high blood pressure .Because daidzein has poor water solubility and fat solubility, it can only be made into oral dosage form in clinical application and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36A61K31/353A61P35/00
Inventor 彭游邓泽元熊冬梅
Owner NANCHANG UNIV
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