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Method for synthesizing tanshinol

A synthesis method and technology of danshensu are applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylate and other directions, which can solve the problems of singleness and lack of optical activity, and achieve the effects of easy availability of raw materials and simple operation.

Inactive Publication Date: 2011-08-17
JINAN UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Tong Yuanfeng et al. used 3,4-dihydroxybenzaldehyde as the starting material, and went through six steps of benzyl protection, Darzens reaction, Lewis acid selective ring opening, NaBH4 reduction, NaOH hydrolysis, and hydrogenation. But in the end no optically active single enantiomer was obtained
[0006] So far no pure R-(+)-β-(3, 4-dihydroxy A report on the synthetic method of phenyl) lactic acid (danshensu)

Method used

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  • Method for synthesizing tanshinol
  • Method for synthesizing tanshinol
  • Method for synthesizing tanshinol

Examples

Experimental program
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Effect test

Embodiment 1

[0030] ( R )-3-(3-acetyl-4-hydroxyphenyl)-2-alanine synthesis:

[0031] Take a 250mL three-neck flask, add 175 mL of nitrobenzene to it, add (7.2 g, 40 mmol) of D-tyrosine at room temperature, then add aluminum trichloride, and add acetyl chloride to the reaction system at one time after stirring (57.3 mmol), the reaction system was gradually heated to 85-90 ° C, reacted for 4-8 h, then poured the mixed solution into the mixed solution of concentrated HCl and ice, removed the organic layer, kept the water layer, and washed the water layer with ethyl acetate The ester was extracted 3 times (50 mL×3), the aqueous layer was crystallized at low temperature, and the precipitated crystals were recrystallized with 5mol / L to finally obtain the compound ( R )-3-(3-acetyl-4-hydroxyphenyl)-2-alanine, beige crystal. m.p 208-214°C, the melting point of the product is consistent with that of known compounds; MS (ESI) [M+H] + m / z 224.2.

Embodiment 2

[0033] ( R )-3-(3-butyryl-4-hydroxyphenyl)-2-alanine synthesis:

[0034] Take a 250 mL three-neck flask, add 175 mL of nitrobenzene to it, add (7.2 g, 40 mmol) of D-tyrosine at room temperature, then add aluminum trichloride, and add butyryl chloride to the reaction system at one time after stirring (57.3 mmol), the reaction system was gradually heated to 85-90 ° C, reacted for 4-8 h, then poured the mixed solution into the mixed solution of concentrated HCl and ice, removed the organic layer, kept the water layer, and washed the water layer with ethyl acetate The ester was extracted 3 times (50 mL×3), the aqueous layer was crystallized at low temperature, and the precipitated crystals were recrystallized with 5mol / L to finally obtain the compound ( R )-3-(3-butyryl-4-hydroxyphenyl)-2-alanine. (4.6 g, 42% yield), solid. The mass spectrum of the product is consistent with that of known compounds.

Embodiment 3

[0036] ( R )-3-(3-hexanoyl-4-hydroxyphenyl)-2-alanine synthesis:

[0037] Take a 250mL three-necked flask, add 88 mL of nitrobenzene to it, add (3.6 g, 20 mmol) of D-tyrosine at room temperature, then add aluminum trichloride, and add acetyl chloride to the reaction system at one time after stirring (2 mL, 29 mmol), the reaction system was gradually warmed up to 85-90 °C, and reacted for 4-8 h, then poured the mixed solution into the mixed solution of concentrated HCl and ice, removed the organic layer, kept the water layer, and the water layer Extracted 3 times with ethyl acetate (25 mL×3), the aqueous layer was crystallized at low temperature, and the precipitated crystals were recrystallized with 5mol / L to finally obtain the compound ( R )-3-(3-hexanoyl-4-hydroxyphenyl)-2-alanine (2.5 g, 44.8% yield). The mass spectrum of the product is consistent with that of known compounds.

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Abstract

The invention discloses a method for synthesizing tanshinol, which comprises the following steps of: 1) performing Friedel-Crafts acylation reaction on R-tyrosine serving as a raw material and an acylation reagent under the catalytic condition of Lewis acid; 2) performing diazotization reaction on the product in the step 1) and sodium nitrite or potassium nitrite under the catalytic condition of acid; and 3) performing Dakin reaction on the product in the step 2) and a peroxide under the action of alkali to obtain the tanshinol, wherein the reaction equation is shown as (3). In the synthesizing method, the raw materials are easily obtained, the operation is simple, and large-scale industrialized production is suitable.

Description

technical field [0001] The invention relates to a synthesis method of danshensu. Background technique [0002] Danshensu is one of the important water-soluble active components of the traditional Chinese medicine Salvia miltiorrhiza, and its structure is ( R )-3-(3,4-dihydroxyphenyl)-2-hydroxypropionic acid, whose structural formula is shown in (I): [0003] [0004] In the structure of Danshensu, the carbon atom at the α-position of the carboxyl group is chiral, and the natural Danshensu is in the R configuration. It has been reported in the literature that Danshensu can dilate coronary arteries, inhibit platelet aggregation, improve microcirculation, reduce the range of myocardial infarction in rats and alleviate the condition, and can inhibit the reactions caused by hydroxyl radicals, superoxide ions and nitrite radicals, which is a good Antioxidants, etc. In clinical practice, Danshensu injection is often used to treat coronary heart disease, angina pectoris and oth...

Claims

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Application Information

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IPC IPC(8): C07C59/52C07C51/367
Inventor 王玉强于沛王磊陈永红续倩赵增超程潜任俊兰
Owner JINAN UNIVERSITY
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