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A preparing method and uses of mangostin and mangostin analogues

A technology for mangostin and its analogues, which is applied in the field of acid sphingomyelinase inhibitors, preparation of mangostin analogues, and sunscreen agents, and can solve the problems of low yield, harsh reaction conditions, and high reaction costs

Active Publication Date: 2017-04-05
南京美竹医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are some defects in the above synthesis method: long reaction steps, harsh reaction conditions, extremely low yield, high cost of most reactions, difficult to obtain reaction raw materials, and difficult to be applied to large-scale production

Method used

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  • A preparing method and uses of mangostin and mangostin analogues
  • A preparing method and uses of mangostin and mangostin analogues
  • A preparing method and uses of mangostin and mangostin analogues

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Preparation of 3,6-dimethoxy-1,7-dihydroxy-2,8-diprenyl-9H-xanthone

[0027] Dissolve 2 g (5.43 mmol) of 3,6-dimethoxy-1,7-dihydroxy-2,8-allyl-9H-xanthone in 3 mL of anhydrous dichloromethane, and add 15 mg of 1,3 -Bis(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(dichlorobenzylidene)(tricyclohexylphosphine)ruthenium, 6.1 mL (51 mmol) 2-methyl- 2-Butene, under nitrogen protection, reacted at 50°C for 4h, stopped the reaction, concentrated, and purified by column chromatography to obtain 1.5g of yellow solid 3,6-dimethoxy-1,7-dihydroxy-2,8-di Isopentenyl-9H-xanthone, yield 65%.

[0028] 1 H NMR (300MHz, CDCl 3 ): δ1.64 (6H, s, -CH 3 ×2), δ1.68 (6H, s, -CH 3 ×2), δ3.35 (2H, d, J=6.9Hz, -CH 2 -), δ3.90 (3H, s-OCH 3 ), δ3.99 (3H, s-OCH 3 ), δ4.15 (2H, d, J=6.7Hz, -CH 2 -), δ5.23(2H, m, -CH=×2), δ6.30(1H, s, Ar-H), δ6.71(1H, s, Ar-H), δ13.5(1H, s, Ar-OH); ESI-MS (m / z): 424 [M+H] + .

Embodiment 2

[0029] Embodiment 2: Preparation of β-methoxy-mangostin

[0030] Dissolve 410 mg (1 mmol) of 3,6-dimethoxy-1,7-dihydroxy-2,8-diprenyl-9H-xanthone in 30 mL of acetone, add 276 mg (2 mmol) of potassium carbonate, Dimethyl sulfate 0.142mL (1.5mmol), reflux for 2h, spin dry the solvent under reduced pressure, add 25mL of 10% sodium hydroxide solution, reflux for 1h, cool to room temperature, add dilute hydrochloric acid to adjust the pH value to about 3, dichloromethane Extracted three times, dried, and separated and purified by column chromatography to obtain 392 mg of yellow solid β-methoxy-mangostin with a yield of 89.5%.

[0031] 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, d, J=6.0Hz, -CH 2 -), δ5.13(2H, m, -CH=×2), δ6.56(1H, s, Ar-H), δ7.04(1H, s, Ar-H), δ13.5(1H, s, Ar-OH); ESI-MS (m / z): 439 [M+H] + .

Embodiment 3

[0032] Example 3: Preparation of α-mangostin

[0033] Add 1g (41.7mmol) of sodium hydride and 12mL of DMF to a three-necked flask, add 8.3mL (91.3mmol) of 1-propanethiol under nitrogen protection, stir at room temperature for 5min and all the solids dissolve, add 1g (2.28mmol) of β- 15 mL of DMF solution of methoxy-mangostin, heated to reflux under nitrogen protection, cooled to room temperature after 6 hours, added 10% hydrochloric acid to adjust the reaction solution to acidity, then added 50 mL of water to dilute, extracted with ethyl acetate, dried, and column layer Analyze and purify, obtain 0.56g yellow powdery solid α-mangostin, yield 60%;

[0034] 1 H NMR (300MHz, CDCl 3 ): δ1.70, 1.78, 1.84, 1.85 (3H each, s, -CH 3 ), δ3.46, 4.10 (2H, d, J=7.0Hz, J=5.9Hz, -CH 2 -), δ3.81 (3H, s, -OCH 3 ), δ5.27 (2H, m, -CH=×2), δ6.30, 6.83 (1H, s, Ar-H), δ13.78 (1H, s, C 1 -OH); HR-EIMS (m / z): 410.1728.

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Abstract

The invention belongs to the fields of innovative medicines and cosmetics and particularly relates to a preparing method and uses of mangostin shown as a formula (I) and mangostin analogues shown as a formula (II). Alpha-mangostin, beta-mangostin, gamma-mangostin and analogues thereof are respectively prepared through olefination and through controlling conditions for deprotection. According to the method, products are high in purity, operation is simple and convenient, yields are high, costs are low and the method is suitable for large-scale production. On one hand, the beta-mangostin, the gamma-mangostin, beta-methoxy-mangostin, and analogues thereof have ultraviolet absorption ability and ultraviolet light radiation preventing functions so that the beta-mangostin, the gamma-mangostin, the beta-methoxy-mangostin, and the analogues thereof can be adopted as a sun-screening agent separately or compounded with other sun-screening agents and applied into cosmetics; and on the other hand, the beta-mangostin, the gamma-mangostin, the beta-methoxy-mangostin, and the analogues thereof have activity of inhibiting acid sphingomyelinase so that the beta-mangostin, the gamma-mangostin, the beta-methoxy-mangostin, and the analogues thereof can be adopted as acid sphingomyelinase inhibitors and applied for preparation of medicines for preventing and treating acid sphingomyelinase related diseases mainly including cardio cerebrovascular diseases, neurological diseases, liver diseases, lung diseases, autoimmune diseases, infectious diseases and the like.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and cosmetics, and in particular relates to a preparation method of mangostin represented by formula (I) and a mangostin analog represented by formula (II) and its use as a sunscreen agent, acid sphingomyelinase Use of Inhibitors. [0002] Background technique [0003] Mangosteen (Garcinia mangostana Linn.) is a tropical plant with high nutritional and medicinal value. It is widely distributed in Southeast Asia. It has been used as traditional Chinese medicine for many years to treat abdominal pain, diarrhea, leukemia, sepsis and other diseases. Mangosteen peel contains a large number of biologically active substances, and mangostin is an important class of biologically active substances in mangosteen peel, because it has anticancer, antibacterial, antimalarial, antiviral, neuroprotective, hypoglycemic, etc. The pharmacological activity has attracted much attention, mainly including α-mangos...

Claims

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Application Information

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IPC IPC(8): C07D311/86A61K8/49A61Q17/04A61K31/352A61P9/10A61P25/24A61P25/28A61P1/16A61P11/00A61P25/00A61P19/02A61P29/00A61P37/02A61P31/04A61P31/16A61P1/00A61P31/00A61P35/00A61P3/10
CPCA61K8/498A61K31/352A61Q17/04C07D311/86
Inventor 王进欣杨侃
Owner 南京美竹医药科技有限公司
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