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Novel synthesis method of mangostin

A mangostin, a new synthesis technology, applied in the direction of organic chemistry, etc., can solve the problems of long cycle, cumbersome steps, low yield and so on

Inactive Publication Date: 2014-06-18
CHINA PHARM UNIV
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  • Description
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Problems solved by technology

[0004] At present, mangostin is mainly obtained through two ways: 1), extracting from natural mangosteen peel, but the current extraction method has cumbersome steps, long cycle and low yield (3.74%, CN101525328A); 2), through fully synthetic or semi-synthetic method to obtain

Method used

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  • Novel synthesis method of mangostin

Examples

Experimental program
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Effect test

Embodiment 1

[0046] Preparation of 1,7-(1,1-dimethyl-allyloxy)-3,6-dimethoxy-9H-xanthone (IV):

[0047] Dissolve 330 mg (1.15 mmol) of 1,7-dihydroxy-3,6-dimethoxy-9H-xanthone (III) in 40 ml of acetone, add 256 mg (4.58 mmol) of potassium hydroxide and 10 mg of potassium iodide in sequence, 3-Chloro-3-methyl-1-butene (II), refluxed for 12 hours, and after suction filtration, column chromatography (petroleum ether: ethyl acetate = 4: 1) gave yellow powdery solid 1,7-(1 , 1-dimethyl-allyloxy)-3,6-dimethoxy-9H-xanthone (IV) 414 mg, yield 85.2%.

[0048] 1 H-NMR (300MHz, CDCl 3 ): δ1.68 (9H, s, -CH 3 ×3), δ1.76 (3H, s, -CH 3 ), δ3.93, 3.97 (3H each, s, -OCH 3 ×2), δ4.64(4H, d, =CH 2 ×2), δ5.54, 6.64 (1H each, t, -CH=×2), δ6.32, 6.44, 6.79, 7.67 (1H, s, C 2 , C 4 , C 5 , C 8 -H), δ13.78 (1H, s, C 1 -OH);

[0049] ESI-MS (m / z): 437[M+Na] + .

Embodiment 2

[0051] Preparation of 1,7-dihydroxy-3,6-dimethoxy-2,8-prenyl-9H-xanthone (V):

[0052] Dissolve 424 mg (1 mmol) of 1,7-(1,1-dimethyl-allyloxy)-3,6-dimethoxy-9H-xanthone (IV) in 15 ml of N,N-dimethyl To aniline, add anhydrous aluminum chloride 10mg, N 2 Heat up under protection, reflux for 4 hours, cool to room temperature, add 15% HCl and stir for 20 min, extract with ethyl acetate, combine organic phases, wash once with 10% HCl, and dry over anhydrous sodium sulfate. After column chromatography (petroleum ether: ethyl acetate = 8:1), yellow solid 1,7-dihydroxy-3,6-dimethoxy-2,8-diprenyl-9H-xanthone was obtained (V) 276 mg, yield 65.1%.

[0053] 1 H NMR (300MHz, DMSO-D6): δ1.64 (6H, s, -CH 3 ×2), δ1.79 (3H, s, -CH 3 ), δ1.89 (3H, s, -CH 3 ), 3.34 (2H, d, J=9.12Hz, -CH 2 -), δ3.79~4.14 (6H, t, -OCH 3 ×2), δ4.12 (2H, m, -CH 2 -), δ5.18(2H, m, -CH=×2), δ6.57(1H, s, Ar-CH), δ6.73(1H, s, Ar-CH), δ9.12(1H, s, Ar-OH), δ13.4 (1H, s, Ar-OH);

[0054] EI-MS (m / z): 424[M] + ....

Embodiment 3

[0056] Preparation of 1-hydroxy-3,6,7-trimethoxy-2,8-diprenyl-9H-xanthone (β-mangostin-OMe) (VI):

[0057] Dissolve 300 mg (0.707 mmol) of 1,7-dihydroxy-3,6-dimethoxy-2,8-diprenyl-9H-xanthone in 30 ml of acetone, and add 195 mg of potassium carbonate (1.41 mmol), dimethyl sulfate 161mg (1.272mmol), reflux reaction for four hours, evaporate the solvent under reduced pressure, add 10% NaOH solution and reflux for 1 hour, cool to room temperature, adjust pH to acidity, extract three times with ethyl acetate, combine organic phase, dried over anhydrous sodium sulfate, and separated by column chromatography (petroleum ether: ethyl acetate = 8:1), to obtain 1-hydroxyl-3,6,7-trimethoxy-2,8-diisoamyl as a yellow oil Alkenyl-9H-xanthone (VI) 287 mg, yield 92.6%.

[0058] mp: 116-118°C;

[0059] 1 H NMR (300MHz, DMSO-D6): δ1.72 (6H, s, -CH 3 ×2), δ1.77 (6H, s, -CH 3 ×2), δ3.28(2H, d, J=7.2Hz, -CH 2 -), δ3.68 (3H, s-OCH 3 ), δ3.90 (3H, s-OCH 3 ), δ3.96 (3H, s-OCH 3 ), δ4.02 (2H,...

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Abstract

The invention belongs to the field of chemical synthesis and particularly relates to a novel synthesis method of mangostin as shown in the formula (I), wherein the mangostin as a natural effective component has favorable anti-tumor activity, cardiovascular activity, antioxidant activity, anti-inflammatory activity, antibacterial activity and other pharmacological activities. The novel synthesis method comprises the steps: with 1, 7-dihydroxyl-3, 6-dialkoxyl-9H-xanthenone as a raw material, sequentially carrying out nucleophilic substitution, Claisen rearrangement, alkylation, deprotection and the like to obtain alpha-mangostin, beta-mangostin, belt-mangostin-OMe and gamma-mangostin. The novel synthesis method is simple in step and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to a new synthesis method of mangostin, a natural product represented by formula (I), which has good anti-tumor activity, cardiovascular activity, anti-oxidation, anti-inflammatory and antibacterial activities. [0002] Background technique [0003] The peel and bark of mangosteen (Garcinia mangostana L) are used as traditional Chinese medicine by residents in the tropical regions of Southeast Asia to treat fever, dysentery, wound infection and other diseases, and the fruit has rich nutritional value, known as the "king of fruits" (phytochemistry. 1997, 44: 191-214; J Agric Food Chem. 2002, 50: 7449-7454; J Agric Food Chem. 2007, 55: 7689-7694). α-mangostin, β-mangostin, β-OMe-mangostin and γ-mangostin are the main biologically active compounds isolated from mangosteen husk, among which α-mangostin has the most content and strong biological activity. A large number o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/86
CPCC07D311/86
Inventor 王进欣苗光强杨侃顾勤兰崔博黄志鹏
Owner CHINA PHARM UNIV
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