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A 1,3,6,7-tetrahydroxyxanthone derivative and its preparation method and use

A technology of tetrahydroxyxanthone and derivatives, applied in the field of acid sphingomyelinase inhibitors, sunscreen agents, 1, can solve the problem of insufficient inhibitory activity

Active Publication Date: 2020-10-02
CHINA PHARM UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the research group has used α-mangostin as the lead compound to modify the structure, but the inhibitory activity of xanthone derivatives on acid sphingomyelinase is not as good as that of α-mangostin

Method used

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  • A 1,3,6,7-tetrahydroxyxanthone derivative and its preparation method and use
  • A 1,3,6,7-tetrahydroxyxanthone derivative and its preparation method and use
  • A 1,3,6,7-tetrahydroxyxanthone derivative and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1: Preparation of (trans, trans)-3,6-dimethoxy-1,7-dihydroxy-2,8-bis-(2-heptenyl)-9H-xanthone (I-1 )

[0052] Dissolve 2 g (5.43 mmol) of 3,6-dimethoxy-1,7-dihydroxy-2,8-diallyl-9H-xanthone in 3 mL of anhydrous dichloromethane, add 1,3 -Bis(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(dichlorobenzylidene)(tricyclohexylphosphine)ruthenium 15mg, 1-hexene 13.6mL (108.6mmol ), under the protection of nitrogen, reacted at 50°C for 4h, stopped the reaction, concentrated, and purified by column chromatography to obtain 1.82g of yellow solid I-1 with a yield of 70%.

[0053] 1 H NMR (300MHz, CDCl 3 ): δ0.85, 0.93 (3H each, s, -CH 3 ), δ1.31 (8H, m, -CH 2 CH 2 -×2), δ1.95 (4H, m, -CH 2 ×2), δ3.35 (2H, d, J=6.9Hz, -CH 2 -), δ3.90 (3H, s-OCH 3 ), δ3.99 (3H, s-OCH 3 ), δ4.14 (2H, d, J=6.7Hz, -CH 2 -), δ5.54(4H, m, -CH=×4), δ6.31(1H, s, Ar-H), δ6.73(1H, s, Ar-H), δ13.5(1H, s, Ar-OH); ESI-MS (m / z): 481 [M+H] + .

Embodiment 2

[0054] Embodiment 2: Preparation (anti)-4-[2,3,6-trimethoxy-8-hydroxyl-7-[(anti)-3-carboxy-2-propenyl]-2-butenoic acid (I -6)

[0055]Dissolve 2 g (5.23 mmol) of 3,6,7-trimethoxy-1-hydroxy-2,8-allyl-9H-xanthone in 3 mL of anhydrous dichloromethane, add 1,3-bis( 2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(dichlorobenzylidene)(tricyclohexylphosphine)ruthenium 15mg, acrylic acid 14.4mL (209.2mmol), under nitrogen protection, React at 50°C for 4h, stop the reaction, concentrate, and purify by column chromatography to obtain 2.07g of yellow solid I-6 with a yield of 82%.

[0056] 1 H NMR (300MHz, DMSO), δ3.25 (2H, d, J=6.48Hz, -CH 2 -), δ3.38, 3.87, 3.92 (3Heach, s, -OCH 3 ), δ4.02 (2H, s, -CH 2 -), δ4.85 (2H, d, J=15.06Hz, -CH=×2), δ5.57 (1H, m, -CH=), δ6.58 (1H, m, Ar-H), δ6 .76(1H, m, -CH=), δ7.06(1H, m, Ar-H), δ12.08(1H, s, -COOH), δ13.5(1H, s, -COOH); ESI -MS(m / z): 471[M+H] + .

Embodiment 3

[0057] Example 3: 3,6,7-trimethoxy-1-hydroxyl-2,8-di-[(trans, trans)-4-methyl-4-hydroxyl-2-pentenyl]-9H-xanyl Xanthone (I-7)

[0058] Dissolve 2 g (5.23 mmol) of 3,6,7-trimethoxy-1-hydroxy-2,8-allyl-9H-xanthone in 3 mL of anhydrous dichloromethane, add 1,3-bis( 2,4,6-Trimethylphenyl)-2-(imidazolidinylidene)(dichlorobenzylidene)(tricyclohexylphosphine)ruthenium 15mg, 2-methyl-3-butene-2- Alcohol 11mL (104.6mmol), reacted at 50°C for 4h under nitrogen protection, stopped the reaction, concentrated, and purified by column chromatography to obtain 1.95g of yellow solid I-7 with a yield of 75%.

[0059] 1 H NMR (300MHz, CDCl 3 ): δ1.04(2H, s, -CH×2), δ1.22(12H, s, -CH 3 ×4), δ3.81 (2H, d, J=5.43Hz, -CH 2 -), δ3.51 (2H, d, J=5.7Hz, -CH 2 -), δ3.74 (3H, s-OCH 3 ), δ3.92, 3.96 (3Heach, s-OCH 3 ), δ5.64, 5.74 (2H, m, -CH=×2), δ6.81 (1H, s, Ar-H), δ7.5 (1H, s, Ar-H), δ13.07 (1H , s, Ar-OH); ESI-MS (m / z): 497 [M-H] - .

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Abstract

The invention belongs to the field of innovative drugs and cosmetics, and particularly relates to a 1,3,6,7-tetrahydroxy xanthone derivative shown in the formula (I) and the formula (II) and a preparing method and application of the derivative to medicine and cosmetics. The derivative is prepared through an olefination reaction. An ultraviolet spectrophotometer is adopted to measure the ultraviolet absorption spectrum of the compound in the 280-400 nm ultraviolet interval, and the result shows that the 1,3,6,7-tetrahydroxy xanthone derivative has ultraviolet absorption capacity and the ultraviolet radiation resisting function and can be applied to cosmetics serving as a sun-screening agent or being compounded with other sun-screening agents. The result of in-vitro acid sphingomyelinase inhibitory activity tests shows that the compound has acid sphingomyelinase inhibitory activity and can be applied to preparation of drugs for preventing and treating diseases related to acid sphingomyelinase serving as an acid sphingomyelinase inhibitor, wherein cardiovascular and cerebrovascular diseases, nervous system diseases, hepatic diseases, lung diseases, autoimmune diseases, infectious diseases, cancers and the like are mainly involved.

Description

technical field [0001] The invention belongs to the field of pharmaceutical chemistry and cosmetics, and specifically relates to 1,3,6,7-tetrahydroxyxanthone derivatives represented by formula (I) and formula (II) and their preparation methods and their use as sunscreens and acid sheaths Use of phospholipase inhibitors. [0002] Background technique [0003] Ultraviolet radiation is the number one killer of the skin. Skin photoaging, wrinkles, skin allergies, dry skin, skin cancer and various other skin diseases are directly related to ultraviolet radiation. Especially in recent years, with the continuous destruction of the ozone layer, the shielding effect of the atmosphere on ultraviolet rays has been continuously weakened, and the amount of ultraviolet radiation reaching the earth's surface is increasing day by day, which is more and more harmful to human beings. According to relevant data, when the ozone layer is reduced by 10%, the amount of ultraviolet radiation re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/86A61K31/352A61K8/49A61Q17/04A61P9/10A61P25/24A61P25/28A61P1/16A61P11/00A61P19/02A61P37/02A61P31/04A61P11/02A61P31/16A61P1/00A61P35/00A61P3/10
CPCA61K8/498A61K2800/782A61Q17/04C07D311/86
Inventor 王进欣毕小玲张阔军顾勤兰杨侃
Owner CHINA PHARM UNIV
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