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A kind of curcumin phosphate compound, preparation method and application

A technology of curcumin phosphate and compound, applied in the field of curcumin phosphate compound, can solve the problems of fast metabolism, low bioavailability, poor water solubility and the like

Inactive Publication Date: 2017-10-10
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Although curcumin exhibits certain activity of inhibiting transthyretin protein aggregation, its poor water solubility, fast metabolism and low bioavailability greatly limit its clinical use.

Method used

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  • A kind of curcumin phosphate compound, preparation method and application
  • A kind of curcumin phosphate compound, preparation method and application
  • A kind of curcumin phosphate compound, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083]

[0084] Dissolve 1.84g (0.005mol) of curcumin (0.005mol) and 2.02g (0.02mol) of triethylamine in 30mL of dichloromethane to obtain a solution, lower the solution to 0°C to 5°C, and add dichlorophosphoric acid dropwise while maintaining the temperature Methyl ester 1.45g (0.008mol) in dichloromethane solution 5mL, after the dropwise addition is completed, rise to 20°C and react at this temperature for 24h, stop the reaction to obtain a mixed product, and evaporate the solvent in the mixed product to dryness under reduced pressure to obtain a yellow The oily liquid was subjected to silica gel column chromatography (volume ratio of petroleum ether: acetone = 15:1) to obtain 0.84 g of the product Cur-4 with a yield of 35.1%. Melting point (m.p): 81-83°C. 1 H-NMR (CDCl 3,400MHz)δ:3.890(s,6H),3.903(s,3H),3.916(s,3H),5.816(s,1H),6.464-6.527(m,2H),6.907(d,1H),7.036 -7.113 (m, 4H), 7.287 (d, 1H), 7.546-7.608 (m, 2H); LC-MS m / z: 477 [M+1].

[0085] Dissolve 0.48 g (1 mmol)...

Embodiment 2

[0087] Dissolve 0.45g (1mmol) of Cur-1 prepared in Example 1 in 20mL of ethanol and cool to 0°C to 5°C, keep the temperature and add 0.08g (2mmol) of sodium hydroxide solution 2mL dropwise, and continue the reaction for 30min , the reaction was stopped, and a large amount of yellow solid was precipitated; the solid was filtered and washed with ethanol at 0°C to 5°C to obtain a precipitate, and then the precipitate was vacuum-dried to obtain the product Cur-30.41g, with a yield of 83.3%. m.p.: 160-161°C.

Embodiment 3

[0089] Dissolve 0.48 g (1 mmol) of Cur-4 prepared in Example 1 in 10 mL of acetone, add dropwise 1.00 mL of a solution of 0.23 g (1.50 mmol) of sodium iodide in acetone at 0° C. to 5° C. Stirring at 20°C for 48 hours, a solid precipitate was obtained after the reaction was complete, which was filtered and washed with acetone to obtain 0.37 g of the product Cur-2, with a yield of 75.1%. m.p.: 143-145°C. 1 H-NMR (400Hz, D 2 O)δ: 3.819(s, 3H), 3.882(s, 3H), 3.912(s, 3H), 5.831(s, 1H), 6.406-6.553(m, 2H), 6.825-7.108(m, 5H), 7.269 (d, 1H), 7.525-7.623 (m, 2H); LC-MS m / z: 451 [M-Na].

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Abstract

The invention relates to a curcumin phosphate compound, a preparation method and application, and belongs to the field of medicinal chemistry. The general structural formula of the compound is as follows: X is O or S, and R1 and R2 are independently: (1) a salt formed by substituted phosphoric acid and ions or a salt formed by thiophosphoric acid and ions, and the ions are H+, NH4+ or Metal ions; or (2) salts formed with organic bases; or (3) benzene rings; or (4) straight-chain, branched-chain or cyclic alkane groups with 1 to 10 carbon atoms; or (5) carbon chain A linear, branched or cyclic alkane group with 1 to 10 carbon atoms connected to a benzene ring in the middle or at the end. The compound is obtained through phosphorylation reaction of curcumin and substituted phosphorus oxychloride. The compound has the activity of inhibiting transthyretin aggregation and can be used as a medicine for treating transthyretin-related amyloidosis.

Description

technical field [0001] The present invention relates to a kind of curcumin phosphate compound, preparation method and application, described compound can inhibit transthyretin (transthyretin, TTR) aggregation activity, can be used as the medicine for the treatment of amyloidosis disease related to transthyretin Medicine belongs to the field of medicinal chemistry. Background technique [0002] In 1853, Virchow first discovered the presence of amyloidosis in human diseased tissues, which can be detected by the iodine-sulfuric acid method. Subsequent studies have found that amyloidosis is a series of clinical diseases caused by the deposition of amyloid precursor protein fibers in the intercellular matrix, which leads to the impairment of tissue nucleus function. Alzheimer's disease (AD) caused by β-amyloid aggregation is common, as well as senile systemic amyloidosis (Senile systemic amyloidosis, SSA) and familial amyloid multiples caused by transthyretin (TTR) aggregation ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/12C07F9/18A61K31/683A61K31/661A61K31/6615A61P25/28A61P43/00
Inventor 温鸿亮杨小梅王东阁刘西环
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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