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Method for synthesizing hypericin

A synthetic method and technology of hypericin, applied in chemical instruments and methods, preparation of organic compounds, preparation of quinones, etc., to achieve the effects of high yield, mild reaction conditions and low synthesis cost

Active Publication Date: 2011-09-14
GUANGDONG HINAPHARM PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the deficiencies of the existing synthetic methods, to provide a microwave-assisted synthetic method of hypericin that is simple, low in cost and high in yield

Method used

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  • Method for synthesizing hypericin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] (one). Synthesis of Emodin Anthrone

[0015] Accurately weigh 1.78 g of emodin and 200 ml of glacial acetic acid in a four-neck flask, stir under nitrogen protection, heat up to reflux, and then add 5.86 g of SnCl 2 2H 2 0, and in the whole process of the reaction, slowly dropwise add 30 ml of hydrobromic acid with a mass fraction of 48%. After reacting for 6 h, the stirring and nitrogen protection were stopped. After the solution was cooled, it was suction-filtered, and the filter cake was washed with distilled water until neutral, and dried to obtain 1.48 g of a light yellow powder with a yield of 96.1% and a melting point of 254°C-258°C. During the reaction process, the reaction was tracked by thin-layer chromatography, and the developer used was a mixed solution of benzene-ethanol (v / v, 8:2). IR (potassium bromide compressed tablets), v / cm -1 : 1620 cm -1 ; MS, m / z 255 (M — ); 1 H-NMR (DMSO-d6): δH: 2.33 (s, 3H, Me), 4.31 (s, 2H, CH 2 ), 6.22(d, 1H, J = ...

Embodiment 2

[0021] (one). Synthesis of Emodin Anthrone

[0022] Different from Example 1, the amount of emodin used is 0.83 g, glacial acetic acid is 150 ml, SnCl 2 2H 2 O 3.25 g, hydrobromic acid 20 ml. The reaction time was 4.5 h, and the yield was 86.2%.

[0023] All the other steps are the same as in Example 1.

[0024] (two). Synthesis of Protohypericin

[0025] The difference from Example 1 is that the amount of emodin anthrone used is 1.88 g, potassium tert-butoxide is 0.05 g, and dimethylformamide is 5 ml. The reaction temperature was 130 ℃, the microwave power was 4 W, the reaction was 0.6 h, and the yield was 73.9%.

[0026] All the other steps are the same as in Example 1.

[0027] (three). Synthesis of hypericin

[0028] The difference from Example 1 is that the amount of protohypericin used is 0.88 g, acetone is 500 ml, and n-hexane is 100 ml. The power of the halogen lamp used was 200 W, and the obtained yield was 82.5%.

[0029] All the other steps are the same ...

Embodiment 3

[0031] (one). Synthesis of Emodin Anthrone

[0032] Different from Example 1, the amount of emodin used is 3.55 g, glacial acetic acid is 500 ml, SnCl 2 2H 2 O 12.65 g, hydrobromic acid 100 ml. The reaction time was 5 h, and the yield was 78.5%.

[0033] All the other steps are the same as in Example 1.

[0034] (two). Synthesis of Protohypericin

[0035] The difference from Example 1 is that the amount of emodin anthrone used is 3.22 g, potassium tert-butoxide is 0.76 g, and dimethylformamide is 15 ml. The reaction temperature was 180 ℃, the microwave power was 10 W, the reaction was 0.5 h, and the yield was 68.3%.

[0036] All the other steps are the same as in Example 1.

[0037] (three). Synthesis of hypericin

[0038] The difference from Example 1 is that the amount of protohypericin used is 2.33 g, acetone is 2000 ml, and n-hexane is 200 ml. The power of the halogen lamp used was 100 W, and the yield was 73.2%.

[0039] All the other steps are the same as in Ex...

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Abstract

The invention relates to a method for synthesizing hypericin. In the method, emodin serves as a raw material; emodin anthrone condensation reaction with low yield is optimized by a microwave-assisted synthesis method under the alkaline condition; the microwave heating temperature is 130 to 180 DEG C; and the reaction time is 0.2 to 1 hour. Under the conditions, the yield of the condensation reaction is increased by multiple times compared with that of the conventional method; reaction time is greatly saved; the yield of the reaction at each step is over 80 percent; and the reaction conditionscan meet the kilogram-grade production scale of a targeted compound. The synthetic route and method has the characteristics of high yield, short reaction route, mild reaction conditions, short reaction time, low synthetic cost and the like.

Description

technical field [0001] The present invention relates to the chemical synthesis method of compound, especially relates to the chemical synthesis method of hypericin. Background technique [0002] Hypericin is the most biologically active substance in Hypericum perforatum, and has pharmacological activities such as antiviral, antidepressant and antitumor. In addition, hypericin is also a highly efficient photosensitizer, which can induce tumor cell apoptosis in the photodynamic therapy of tumors. In Europe, hypericin and its various preparations have been widely used in the treatment of depression, AIDS and hepatitis. Although my country is rich in Hypericum perforatum, the content of hypericin in the whole plant is only a few ten thousandths. [0003] At present, there are three main synthetic routes of hypericin. One is to directly synthesize hypericin through a series of reactions using small molecular substances as starting materials, such as using 3,5-dimethylbenzoic ac...

Claims

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Application Information

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IPC IPC(8): C07C50/36C07C46/00
Inventor 梁剑平李兆周王学红尚若峰郭文柱郭志廷郝宝成王曙阳陶蕾
Owner GUANGDONG HINAPHARM PHARMA CO LTD
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