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Garcinol derivative and application thereof

A kind of derivative, the technology of mangosteen, applied in mangosteen derivatives and application fields, can solve the problems of mucosal permeability, unsatisfactory bioavailability, etc., and achieve the effect of good prevention and management of cardiac insufficiency and low toxicity

Active Publication Date: 2018-06-22
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Mangosteen alcohol is a polyisoprenyl benzophenone derivative, which is a yellow crystal compound extracted from the dried peel of Garcinia cambogia. Its chemical structure is similar to that of the antioxidant curcumin. It has obvious chemopreventive effect, and has a good preventive and management effect on cardiac insufficiency caused by chemotherapy, drugs, diseases or lifestyles. It is a promising natural chemopreventive drug, but its permeability to mucosa, biological Utilization is not ideal and needs to be further improved

Method used

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  • Garcinol derivative and application thereof
  • Garcinol derivative and application thereof
  • Garcinol derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Dissolve 56g (0.5mol) of 1,3-cyclohexanedione in 100ml of water, cool to ℃, slowly add 71.5g (0.5mol) of triisopropylamine, then slowly add 82g (0.55mol) of 3, 3-Dimethylallyl bromide, stirred overnight at room temperature. Add 725 mL of 2N NaOH solution to the reaction solution, separate layers, extract the aqueous phase with 300 ml of ethyl acetate, acidify the aqueous phase with glacial acetic acid to pH 3-4, suction filter, and dry without purification. Intermediate (II) was obtained with a yield of 60%. ESI-MS m / z: 181.0 [M+H].

[0021] Take 35.3g (0.196mol) of intermediate (II) and dissolve it in 300ml of acetone, add 116.6g (0.686mol) of isopropyl iodide and 64g (0.784mol) of potassium carbonate. React overnight. The acetone was distilled off under reduced pressure, and 400ml of water and 400ml of trichloromethane were added to the residue to dissolve. The layers were separated and the aqueous phase was extracted with dichloromethane (2x300ml) and dried. Con...

Embodiment 2

[0029] Take 22.3g (0.1mol) of intermediate (Ⅲ) and dissolve it in 100ml of CHCl 3 In, add 7.6g (0.004mol) CuI and 11.7g (0.11mol) Cs 2 CO 3 , cooled to -10°C, added 34.8g (0.11mol) Togni reagent II, reacted for 24h, filtered, concentrated, and purified by silica gel column chromatography to obtain 3-isopropoxy-2-(3-methyl-2-butane Alkenyl)-6-trifluoromethylcyclohex-2-enone (IVb), 67% yield. ESI-MS m / z: 291.1 [M+H].

[0030] 24g (0.1mol) of intermediate (IVa) was changed to 29g (0.1mol) of intermediate (IVb), and other operations were the same as in Example 1 to obtain intermediate (Vb) with a yield of 71%.

[0031] 12.0 g (50 mmol) of intermediate Va was changed to 14.5 g (50 mmol) of intermediate Vb, and other operations were the same as in Example 1 to obtain intermediate VIb with a yield of 84%.

[0032] 25.4g (100mmol) of intermediate VIa was changed to 26.2g (100mmol) of intermediate VIb, and other operations were the same as in Example 1 to obtain compound VIIIb with...

Embodiment 3

[0035] Change 296mg (1.2mmol) 3,4-diacetoxybenzoyl nitrile into 212mg (1.2mmol) 3-methoxy-4-hydroxybenzoyl nitrile, and other operations are the same as in Example 2 to obtain compound (3 ), yield 75%. ESI-MS m / z: 479.2 [M-H].

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Abstract

The invention discloses a garcinol derivative or a pharmaceutically acceptable salt (I) thereof, which comprises a stereoisomer or a tautomer. The invention relates to a preparation method of the compound and a use of the compound in medicine for preventing and managing cardiac insufficiency.

Description

technical field [0001] The invention relates to a garcinol derivative, a preparation method thereof, and an application as a drug for preventing and managing cardiac insufficiency. Background technique [0002] Mangosteen alcohol is a polyisoprenyl benzophenone derivative, which is a yellow crystal compound extracted from the dried peel of Garcinia cambogia. Its chemical structure is similar to that of the antioxidant curcumin. It has obvious chemopreventive effect, and has a good preventive and management effect on cardiac insufficiency caused by chemotherapy, drugs, diseases or lifestyles. It is a promising natural chemopreventive drug, but its permeability to mucosa, biological Utilization is not ideal and needs to be further improved. [0003] The fluorine atom has a great impact on the conformation of the molecule, the binding mode with the receptor, and the physiological activity of the compound through hydrogen bonding and other effects. The van der Waals radius of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/18C07C69/21C07C67/29C07C49/83C07C49/84C07C45/44C07C45/51A61P9/00A61P9/04
CPCC07B2200/07C07C49/83C07C49/84C07C69/18C07C69/21
Inventor 张宝华史兰香刘斯婕
Owner SHIJIAZHUANG UNIVERSITY
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