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Synthetic method of Tenuifoliside B

A technology of acetoxyl and sucrose, applied in the field of chemical synthesis of natural product Tenuifolidise B, can solve the problem of no chemical synthesis of Tenuifolidise B, and achieve the effects of cheap and controllable cost, high yield and mild reaction conditions

Active Publication Date: 2014-04-02
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no report on the chemical synthesis of Tenuifoliadise B

Method used

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  • Synthetic method of Tenuifoliside B
  • Synthetic method of Tenuifoliside B
  • Synthetic method of Tenuifoliside B

Examples

Experimental program
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Effect test

Embodiment 1

[0024] 4-Acetoxy-3,5-dimethoxycinnamic acid ( 7 ) preparation:

[0025] Syringaldehyde ( 2 ) 60.06 g (330 mmol) was dissolved in 360 mL of pyridine, 36.72 g (360 mmol) of acetic anhydride was added, refluxed for 2 hours, cooled to room temperature, and directly put into the next reaction, 500 mL of benzene, 52.00 g of malonic acid (500 mmol), piperidine 5 mL, install a reflux device with a water separator, oil bath, stir to dissolve, and reflux for 3 hours. After completion of the reaction, cool to room temperature, add 1000 mL of saturated sodium bicarbonate solution, stir, separate the water layer, acidify with 6 mol / L hydrochloric acid to a pH value of about 5, filter, rinse the filter cake with 500 ml of water, and dry to obtain White solid 4-acetoxy-3,5-dimethoxycinnamic acid ( 7 ) 56.18 g, yield 64%. Melting point, spectral data, and high-resolution mass spectrometry data of 4-acetoxy-3,5-dimethoxycinnamic acid: melting point 202-204 °C; = +0.2 (c = 1.01, MeOH); 1...

Embodiment 2

[0027] 4-acetoxybenzoic acid ( 6 ) preparation:

[0028] p-Hydroxybenzoic acid ( 3 ) 4.55 g (33 mmol) was dissolved in 30 mL of pyridine, 3.67 g (36 mmol) of acetic anhydride was added, and refluxed for 2 hours. After completion of the reaction, cool to room temperature, add 100 mL of saturated sodium bicarbonate solution, stir, separate the water layer, acidify with 6 mol / L hydrochloric acid to a pH value of about 2, filter, rinse the filter cake with 50 ml of water, and dry to obtain White solid 4-acetoxybenzoic acid ( 6 ) 5.50 g, the yield was 93%. Melting point, spectral data, and high-resolution mass spectrometry data of 4-acetoxybenzoic acid: melting point 191-193 °C; 1 H NMR (500 MHz, CD 3 OD): δ = 8.06 (m, J = 8.5, 2.5 Hz, 2 H), 7.21 (m, J = 8.5, 2.5 Hz, 2 H), 2.29 (s, 3 H) ppm; 13 C NMR (125 MHz, CD 3OD): δ = 170.7, 169.1, 156.1, 132.4 (2 C), 129.6, 123.0 (2 C), 21.0 ppm; HRMS (ESI): 181.0498 (calcd. for C 9 h 9 o 4 [M+H] + 181.0501).

Embodiment 3

[0030] 4-Acetoxy-3,5-dimethoxycinnamic anhydride ( 8 ):

[0031] 4-Acetoxy-3,5-dimethoxycinnamic acid ( 7 ) 31.92 g (120 mmol) was dissolved in 4000 mL of anhydrous ethyl acetate, 16.5 mL (120 mmol) of anhydrous triethylamine was added, cooled in an ice bath, and 5.94 g (20 mmol) of triphosgene was added at 0°C under stirring ), reacted for 10 minutes; reacted at room temperature for 20 minutes. Filter, wash the filter cake with anhydrous ethyl acetate (1000 mL), combine the filtrate and washing liquid, evaporate the solvent, and dry to obtain a white solid 4-acetoxy-3,5-dimethoxycinnamic anhydride ( 8 ), directly into the next reaction without purification, the yield is about 82%.

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Abstract

The invention provides a synthetic method of Tenuifoliside B. Sucrose, syringaldehyde and p-hydroxybenzoic acid are used as the starting materials, and subjected to 6 steps of chemical conversion reactions to realize total synthesis of Tenuifoliside B for the first time. The raw materials of sucrose, syringaldehyde and p-hydroxybenzoic acid employed by the invention are convenient, easily available and at controllable low cost; each step of chemical reaction has mild reaction conditions and is easy to implement and operate in the practical application; each step of chemical reaction has high reaction conversion rate, especially the first three reaction steps have mild reaction conditions, simple operations, high yield, small amount of by-products and total yield at about 22.3%; and the Tenuifoliside B can be directly used for subsequent steps of the synthesis reaction without fine column chromatography purification.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and relates to a chemical synthesis method of natural product Tenuifoliside B with brain protection effect. Background technique [0002] Tenuifoliside B (compound 1) is obtained from the traditional Chinese medicine polygala ( Polygala tenuifolia Willd.) (Yukinobu Ikeya, Ko Sugama, Minoru Okada, Hiroshi Mitsuhashi. Chem. Pharm Bull. ,1991, 39(10), 2600-2605.), is a natural product. The chemical structural formula of the natural product (Tenuifoliside B) is as follows: [0003] [0004] Pharmacological experiment results show that Tenuifoliside B (3-10 mg / kg, p.o. ) can significantly improve the memory deficit induced by scopolamine and sodium cyanide in rats, which is similar to the activity of the positive drug tacrine (Yukinobu I, Shigefumi T, Mitsuo T, Humito K, Kouin T, Takuji Y and Masaki A. Biol. and Pharm. Bulletin. , 2004, 27, 1081-1085.), can be used to prepare anti-senile de...

Claims

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Application Information

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IPC IPC(8): C07H13/08C07H1/00
Inventor 栾连军施琦渊吴永江
Owner ZHEJIANG UNIV
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