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Chemical synthesis process for hypericin and derivatives thereof

A kind of hypericin, a technology for chemical synthesis, applied in the field of chemical synthesis of compounds and derivatives thereof

Inactive Publication Date: 2006-09-06
LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

All there is bigger defect in above-mentioned synthesis route, therefore urgently needs an economy, easy and simple to operate, reasonable, the chemical synthesis route of hypericin with relatively higher yield

Method used

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  • Chemical synthesis process for hypericin and derivatives thereof
  • Chemical synthesis process for hypericin and derivatives thereof
  • Chemical synthesis process for hypericin and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The synthesis of embodiment 1, hypericin

[0053] Now use the method of the present invention to artificially synthesize hypericin, and concrete process comprises the following steps:

[0054] 1) Synthesis of acetoacetaldehyde

[0055] The chemical equation for the synthesis of acetoacetaldehyde is as follows:

[0056] The specific method is: mix 18.5g (0.25mol) of ethyl formate and 17.4g (0.30mol) of acetone, slowly drop into 125mL of anhydrous ether containing 6g (0.15mol) of freshly cut sodium wire, and stir under the condition of avoiding water. , After the sodium wire reaction is complete, place it for 12-24h. The gray-yellow solid precipitate was filtered out, washed with anhydrous ether, and dried in vacuo to obtain 17.1 g of solid acetoacetaldehyde. After determination, the yield of acetoacetaldehyde was 80%.

[0057] 2) Synthesis of 2-hydroxyl-4-methylbenzoic acid

[0058] The chemical equation for the synthesis of 2-hydroxy-4-methylbenzoic acid is as fo...

Embodiment 2

[0082] Embodiment 2, the synthesis of hypericin heterocyclic derivatives

[0083]

[0084] Now taking the hypericin heterocyclic derivatives with the above chemical structural formula as an example, the synthetic method of hypericin heterocyclic derivatives is illustrated, that is, to synthesize its corresponding emodin heterocyclic derivatives first, and then obtain The target product of above-mentioned structural formula, concrete process comprises the following steps:

[0085] 1) Synthesis of 1,3,8-trihydroxy-6-benzimidazolone

[0086] Dissolve 166.6 mg of 1,3,8-trimethoxy-6-benzimidazole anthraquinone (0.402 mmol) in 30 mL of glacial acetic acid, and then add 725.6 mg of SnCl 2 .2H 2 The mass percent concentration of O (3.216mmol) is 45% of HBr15mL, filled with argon, refluxed at below 125°C for 1.3 hours, cooled, added to ice water, separated, and the residue was washed with water and vacuum-dried to obtain 130.2mg of product by weight. The yield was 90%. Instrumen...

Embodiment 3

[0089] Embodiment 3, the synthesis of hypericin sulfonic acid derivatives

[0090] R 1 = H or SO 3 H; R 2 = H or SO 3 h

[0091] Now taking the hypericin sulfonic acid derivatives with the above chemical structural formula as an example, the synthetic method of the hypericin sulfonic acid derivatives is illustrated, and the specific method is as follows:

[0092] 1. Synthesis of 2,5-disulfonic acid genserin

[0093] React 45mg of hypericin (0.089mmol) and 105mg of oleum (1.07mmol) at room temperature for 2 hours, dilute with ice water, add sodium chloride until saturated, centrifuge, wash the precipitate with cold water until neutral, and dry in vacuo. Eluted on Sephadex-LH O column, eluent is aqueous methanol (methanol: water=4: 1), obtains 2,5-disulfonic acid aristorin 8mg, productive rate is 10%; The product is carried out instrumental analysis , the result H 1 NMR (DMSO-d 6 , 500MHz, ppm): 15.00(s, 2H), 14.36(s, 2H), 13.51(s, 2H), 7.48(s, CH-9, 12), 2.74(s, 6H,...

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Abstract

The invention discloses a method for chemosynthesis of the hypericin and its derivant. The said method includes the following steps: 1) dissolving 1, 3, 8-trihydroxy-6-methyl anthraquinone in the analytical pure glacial acetic acid,then adding concentrated hydrochloric acid with 36-40 % of zinc bichloride dehydrate, reacting for 1-4 hours at the temperature of less than 125 DEG C, cooling, and obtaining the 1, 3, 8-trihydroxy-6-methyl anthranone; 2) making 1, 3, 8-trihydroxy-6-methyl anthranone, pyridine, piperidine, nitrogen-oxygen pyridine and ferrisulphas hepthydrate react free of light for 0.5-3 hours at the temperature of 100-130 DEG C, then dissolving the reaction products in the acetone, illuminating them by a halogen lamp for 12-24 hours, thickening and dissolving them in the skellysolve B, filtering the deposition, and obtaining the hypericin. The method has advantages of that its operation is simple and reasonable, its cost is cheap, its productivity is high, its actual applied value is higher, so its actual value is broad.

Description

technical field [0001] The invention relates to a chemical synthesis method of a compound and its derivatives, in particular to a chemical synthesis method of hypericin and its derivatives. Background technique [0002] Hypericin (hypericin, 4,4,5,5,7,7-hexahydroxy-2,2-dimethyl-middle-naphthodianthrone, chemical structural formula see formula 1), is Hypericum perforatum ( The most biologically active substance in Hypericum perforatum L.), with antiviral, antidepressant and photokinetic activity. [0003] Since the content of hypericin in the whole plant of Hypericum perforatum is only about 4 / 10,000, at present, the content of hypericin extracted from Hypericum perforatum in its extracts at home and abroad does not exceed 1%. Therefore, Even if the extraction process is improved, the content of hypericin extracted and separated is not very high, and it will destroy a large amount of natural vegetation or occupy a large amount of cultivated land. In order to increase the co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/00C07C49/727
Inventor 梁剑平白卫兵车清明邢桂珍孙瑶
Owner LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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