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Preparation method and application of a class of baicalein-7-methyl ether derivatives

A technology of baicalein and derivatives, applied in the field of medicine, can solve the problem of low activity, and achieve the effects of easy handling, easy availability of materials and low cost

Active Publication Date: 2019-05-14
FUJIAN MEDICAL UNIV UNION HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, studies have shown that baicalein-7-methyl ether has anti-leukemic activity, but the activity is not high (IC 50 ≈40μM)

Method used

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  • Preparation method and application of a class of baicalein-7-methyl ether derivatives
  • Preparation method and application of a class of baicalein-7-methyl ether derivatives
  • Preparation method and application of a class of baicalein-7-methyl ether derivatives

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0042] Compounds IIIb and IIIc were prepared similarly to compound IIIa, substituting 3-bromopropyne for benzyl bromide.

[0043] Compound IIIb: 1 H NMR (400MHz, CDCl 3 )δ12.73(s, 1H), 7.88–7.84(m, 2H), 7.55–7.48(m, 5H), 7.35(t, J=7.2Hz, 2H), 7.30(d, J=7.1Hz, 1H ), 6.65(s, 1H), 6.51(s, 1H), 5.12(s, 2H), 3.89(s, 3H). 13 C NMR (101MHz, CDCl 3 )δ182.79, 163.97, 159.27, 153.46, 153.34, 137.56, 131.90, 131.46, 131.37, 129.17, 128.64, 128.28, 128.07, 126.31, 106.30, 105.66, 90.69, 74.93 for ms C 23 h 19 o 5 [M+H] + 375.1227, found: 375.1226.

[0044] Compound IIIc: 1 H NMR (400MHz, CDCl 3 )δ7.89(dd, J=6.2, 2.5Hz, 2H), 7.69–7.65(m, 2H), 7.53–7.49(m, 3H), 7.47–7.43(m, 2H), 6.83(s, 1H) , 6.70(s, 1H), 5.16(s, 2H), 5.04(s, 2H), 3.94(s, 3H); 13 C NMR (101MHz, CDCl 3 )δ177.30,161.26,158.24,154.86,139.79,137.27,137.21,131.69,131.37,129.44,129.07,128.79,128.39,128.36,128.17,113.42,108.48,96.68,75.96,56.35;Melting Point:125.1-126.3℃ ;HRMS(m / z): calcd for C 30 h 25 o 5 [M+H] ...

Embodiment 1

[0057] Example 1: Inhibitory Effects of Compounds on Tumor Cell Proliferation and Survival

[0058] Material: leukemia cells HL-60.

[0059] Drugs to be tested: compounds at 5 concentrations of 0, 5 μM, 10 μM, 20 μM, and 40 μM.

[0060] The inhibitory effect of compound IIa on the proliferation and survival of leukemia cells HL-60: After HL-60 cells were cultured, the compounds were added and incubated for 48 hours, the proliferation ability of HL-60 cells decreased, and the cells showed apoptosis changes. The results of MTT analysis showed that the survival rate of HL-60 cells showed a downward trend with the increase of IIa concentration (0, 5 μM, 10 μM, 20 μM, 40 μM), and dropped to nearly 70% at 7.24 μM.

Embodiment 2

[0061] Example 2: Effects of Compounds on the Activation of Leukemia Cell Signaling Pathways

[0062] Material: leukemia cells HL-60;

[0063] Drugs to be tested: 4 concentrations of compounds of 0, 5 μM, 10 μM, and 20 μM.

[0064] Effects on the signaling pathway of HL-60 cells: After treating HL-60 cells with IIa for 24 hours, the total protein was extracted and separated by SDS gel electrophoresis. The results of Western blot analysis showed that compound IIa inhibited the activation of Akt signaling pathway in a dose-dependent manner. And activate Caspase-3, thereby inhibiting the proliferation of HL-60 cells and promoting the apoptosis of HL-60 cells.

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PUM

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Abstract

The invention discloses a preparation method and use of baicalein-7-methyl ether derivatives. The baicalein-7-methyl ether derivatives have a general formula shown in the description. In the general formula, R1 represents hydroxyl and R2 represents a C1-C3 straight chain nitrogen-containing compound, a nitrogen-containing heterocyclic compound or an aryl or ester group compound. The baicalein-7-methyl ether derivatives can substantially inhibit leukemia cell propagation and viability and realizes multi-target inhibition of a leukemia cell signal path so that leukemia cell apoptosis is induced and leukemia treatment is realized.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a preparation method and application of a class of baicalein-7-methyl ether derivatives. Background technique [0002] Flavonoids are widely distributed in vegetables, fruits and herbal medicines, and have extremely high medicinal value, such as anti-oxidation, anti-inflammation, anti-tumor, immune regulation, etc., and their development is of great significance. The traditional Chinese medicine Scutellaria baicalensis Georgi was first recorded in "Shen Nong's Materia Medica". It tastes bitter and cold in nature. Baicalin and baicalein (baicalein) are the main flavonoids contained in Scutellaria baicalensis, both of which have a common flavone parent structure. Baicalin and baicalein have various pharmacological activities such as antioxidant, antibacterial, antiviral, antiallergic, antihypertensive, diuretic, and choleretic. In recent years, it has been reported t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C07D311/30A61K31/4192A61K31/5377A61K31/352A61K31/4025A61K31/453A61P35/02
CPCC07D311/30C07D405/12
Inventor 胡建达陈英玉陈海军
Owner FUJIAN MEDICAL UNIV UNION HOSPITAL
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