Calycosin derivative and synthesis method thereof

A synthesis method and product technology, applied in the field of medicine, can solve the problems of unclear target and large effective concentration, achieve good vascular protection effect, and promote the effect of human umbilical vein endothelial cell proliferation

Active Publication Date: 2018-02-02
GUILIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Existing studies have shown that calycosin has the functions of anti-oxidative stress, anti-virus and regulating cell apoptosis, but its disadvantages are that its effective concentration is large and the target is not clear. It can promote the proliferation of ER-positive breast cancer cell MCF-7; although high concentrations of calycosin (>20μM) can inhibit the proliferation of E...

Method used

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  • Calycosin derivative and synthesis method thereof
  • Calycosin derivative and synthesis method thereof
  • Calycosin derivative and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] 1) Take 7-hydroxy-3-(3-hydroxy-4-methoxy)-4H-benzopyran-4-one (300mg) and 1,2-dibromoethane in a molar ratio of 1:8 Dissolve in 13mL of acetone, then adjust the pH of the system to 10 with triethylamine, and react for 8h at room temperature. After the reaction is over, spin dry, add 200ml of ethyl acetate to the residue, and wash with 300mL*3 of water three times. Afterwards, it was dried with anhydrous sodium sulfate and purified on a silica gel column (eluent: ethyl acetate / petroleum ether=1:4, volume ratio) to obtain intermediate product 3 (yield 60%);

[0032] 2) Dissolve intermediate product 3 (100mg) and morpholine in 10mL acetone at a molar ratio of 1:1, adjust the pH of the system to 10 with triethylamine, and react at room temperature for 6 hours. After the reaction is complete, spin-dry it. 150ml ethyl acetate was added to the obtained residue, washed three times with 200ml*3 water, dried with anhydrous sodium sulfate, purified on a silica gel column (eluent: eth...

Embodiment 2

[0039] Repeat Example 1, the difference is that the organic solvent in steps 1) and 2) is changed to DMF. A yellow solid product was obtained (yield 55%).

[0040] The yellow solid product obtained in this example was characterized by nuclear magnetic resonance and determined to be the target compound of the application.

Embodiment 3

[0042] Repeat Example 1, except that the organic solvent in steps 1) and 2) was changed to chloroform. A yellow solid product was obtained (yield 20%).

[0043] The yellow solid product obtained in this example was characterized by nuclear magnetic resonance and determined to be the target compound of the application.

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Abstract

The invention discloses a calycosin derivative and a synthesis method thereof. The derivative is prepared by the steps of: dissolving a compound 1 and a compound 2 in an organic solvent, making the compound 1 and the compound 2 react under a basic condition to obtain an intermediate product 3, and dissolving the intermediate product 3 and a compound 4 in an organic solvent to obtain the targeted crude product. Applicants find that the proliferation of human umbilical vein endothelial cells can be promoted by the derivative of low concentration, so that an effect of good vascular protection isachieved, and therefore the derivative can be applied to the preparation of ERalpha and GPR30 agonists; meanwhile, an inhibitory effect on MCF-7 cells can be generated by the derivative of low concentration (10 uM); the structures of the compound 1, the compound 2, the intermediate product 3 and the compound 4 which are involved in the derivative and the synthesis method of the derivative are shown as follows respectively.

Description

Technical field [0001] The invention relates to a mullein derivative and a synthesis method thereof, and belongs to the technical field of medicine. Background technique [0002] Astragalus is the dry root of Astragalus membranaceus (Fisch.) Bge.Var.mongholicus (Bge) Hsiao or Astragalus membranaceus (Fisch.) Bge. According to the pharmacopoeia, Astragalus is sweet in taste and mild in nature. It can nourish qi and raise yang, replenish health, improve heart function, expand coronary arteries, diuresis and swelling, support sore muscles, antibacterial, antiviral, anti-fatigue, anti-aging, and promote Hematopoietic function, liver protection and other functions. [0003] Calycosin is an isoflavone compound extracted and isolated from Astragalus membranaceus (Ma Xiaofeng et al., Study on Flavonoids in Mongolian Astragalus, Chinese Herbal Medicine, Vol. 36 No. 9, September 2005, p1293-1296 ), its structural formula is as follows: [0004] [0005] Existing studies have shown that mull...

Claims

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Application Information

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IPC IPC(8): C07D311/36A61P9/14A61P35/00
CPCC07D311/36
Inventor 陈健蒋能田晶王勇张幸
Owner GUILIN MEDICAL UNIVERSITY
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