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Preparation method of chrysin amino acid derivative

A technology of chrysin and its derivatives, which is applied in the field of chemistry, can solve the problems of low chrysin derivative utilization, inability to improve the solubility of chrysin, and inability to reduce chrysin, and achieve low investment, significant killing effect, and high yield Effect

Inactive Publication Date: 2017-05-10
NANHUA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The invention provides a chrysin amino acid derivative and a preparation method thereof, aiming at solving the problems that the current c

Method used

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  • Preparation method of chrysin amino acid derivative
  • Preparation method of chrysin amino acid derivative
  • Preparation method of chrysin amino acid derivative

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preparation example Construction

[0030] Such as figure 1 As shown, the preparation method of the chrysin amino acid derivative provided by the embodiment of the present invention, the specific implementation steps include:

[0031] S101. Put 10mmol of chrysin and 11.5mmol of anhydrous potassium carbonate in a 250mL three-necked bottle, add 100mL of solvent acetone, heat and stir under reflux for 1h, then slowly add bromoalkyl to the reaction solution with a constant pressure dropping funnel Carboxylate and catalytic amount of KI 1mmol, continue to condense and reflux at about 60°C, and check the reaction progress by TLC. After the reaction, cool, filter, add appropriate amount of acetone to the filter residue, stir to dissolve and filter again, combine the two filtrates, evaporate the acetone under reduced pressure, and obtain a yellow crude product, which is recrystallized with acetone or separated and purified by silica gel chromatography (eluent: V 石油醚 :V 乙酸乙酯=4:1) to obtain the intermediate product (2 s...

Embodiment 1

[0036] Example 1: Preparation of ethyl 2-(5-hydroxy-2-phenyl-4H-benzopyrone-7-oxo)propionate

[0037]

[0038] Put 10mmol of chrysin and 11.5mmol of anhydrous potassium carbonate in a 250mL three-neck flask, add 100mL of solvent acetone, heat and stir to reflux for 1h, then slowly add 2-bromopropionate ethyl to the reaction solution dropwise with a constant pressure dropping funnel The ester and the catalytic amount of KI1mmol were condensed and refluxed at about 60°C, and the reaction progress was detected by TLC. After the reaction, cool, filter, add appropriate amount of acetone to the filter residue, stir to dissolve and filter again, combine the two filtrates, evaporate the acetone under reduced pressure, and obtain a yellow crude product, which is recrystallized with acetone or separated and purified by silica gel chromatography (eluent: V 石油醚 :V 乙酸乙酯 =4:1) Compound 2 was obtained with a yield of 70.5%. m.p.138.5~140.2℃.IR v max (cm -1 , KBr): 1738, 1657, 1616, 13...

Embodiment 2

[0039] Example 2: Preparation of ethyl 4-(5-hydroxy-2-phenyl-4H-benzopyrone-7-oxo)butanoate

[0040]

[0041] The preparation method was the same as in Example 1, replacing ethyl 2-bromopropionate with ethyl 4-bromobutyrate to obtain compound 3 with a yield of 78.5%. m.p.159~161℃.IRv max (cm -1 , KBr): 1732, 1666, 1612, 1381, 767. 1 H-NMR (400MHz, CDCl 3 ,δppm,J / Hz):1.28(t,J=7.2,3H),2.14~2.17(m,2H),2.53(t,J=7.2,2H),4.09(t,J=6,2H), 4.17(q, J=7.2, 2H), 6.36(d, J=2.0, 1H), 6.49(d, J=2.4, 1H), 6.67(s, 1H), 7.51~7.56(m, 3H), 7.88 (dd,J=1.2,7.6,2H),12.70(s,1H); 13 C-NMR (100MHz, DMSO-d6), δ: 14.08 (C-8"), 23.92 (C-3"), 29.97 (C-4"), 59.88 (C-7"), 67.44 (C-2 ”),92.80(C-8),98.56(C-6),105.12(C-3),105.42(C-10),126.38(C-2',C-6'),129.11(C-3' ,C-5'),130.63(C-4'),132.06(C-1'),157.46(C-9),161.58(C-2),163.18(C-5),164.42(C-7) ,172.39(C-5"),181.87(C-4); ES I-MS, m / z:369.1544[M+H] + .

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Abstract

The invention discloses a chrysin amino acid derivative and a preparation method thereof. The preparation method using chrysin 7 sites to synthesize different series of chrysin derivatives specifically includes: allowing chrysin to have reaction with bromo-alkyl carboxylate, performing hydrolysis to obtain a 7-O-carboxyalkylated chrysin derivative, allowing the 7-O-carboxyalkylated chrysin derivative to have reaction with different types of amino acid alkyl ester, performing amide condensation to obtain a chrysin amino acid alkyl ester type compound, and performing hydrolysis to obtain the chrysin amino acid derivative. The preparation method has the advantages that amino acid is combined with chrysin molecules, and the solubility of the chrysin is improved while the killing effect on normal cells is reduced; the amino acid is the basic unit for forming protein, is an important active molecule in a human body, participates in various life activities and is harmless and nontoxic to the human body; the amino acid is good in solubility, and the demand quantity of tumor cells on the amino acid is higher than that of the normal cells.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and in particular relates to a preparation method of chrysin amino acid derivatives. Background technique [0002] Chrysin's anti-tumor mechanism has attracted people's attention. Studies have shown that chrysin can inhibit tumor cell proliferation, human undifferentiated thyroid cancer cells HTH7 and KAT18 in a dose- and time-dependent manner, and induce lung cancer cell apoptosis. Fluorescence quantitative RT-PCR reaction, colorimetric assay and Wexternblotting analysis The results showed that chrysin induced the apoptosis of lung adenocarcinoma epithelial cells by down-regulating the expression of Bcl-2 family proteins and activating caspase-3 and -9. Related studies have shown that chrysin can also reverse the multidrug resistance of tumor cells. [0003] However, chrysin has poor water-solubility and fat-solubility, little or no intestinal absorption, and the 5 and 7 hydroxyl groups are e...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/352A61P35/00
CPCC07D311/30
Inventor 刘运美何军刘容芳宋秀道
Owner NANHUA UNIV
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