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Water-soluble monodemethoxycurcumin derivative, and preparation method and use of water-soluble derivative

A technology of mono-demethoxy curcumin and methoxy curcumin carboxylic acid, applied in the field of mono-demethoxy curcumin water-soluble derivatives and preparation thereof, can solve the problem of insufficient activity, low bioavailability, water-soluble Sexual problems, etc.

Active Publication Date: 2015-03-25
石磊 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, monodemethoxycurcumin, like curcumin, has the disadvantages of poor water solubility, unstable structure, low bioavailability, and insufficient activity, which limit their application in the field of medicine.

Method used

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  • Water-soluble monodemethoxycurcumin derivative, and preparation method and use of water-soluble derivative
  • Water-soluble monodemethoxycurcumin derivative, and preparation method and use of water-soluble derivative
  • Water-soluble monodemethoxycurcumin derivative, and preparation method and use of water-soluble derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Embodiment 1. Preparation of 3-methoxy-4-(2-carboxyacetoxy)benzaldehyde

[0066]

[0067] Dissolve 5g of vanillin in 100mL of acetone, then add 6.8g of malonic acid to reflux, add 0.5mL of concentrated sulfuric acid during the reflux process, cool overnight, precipitate a solid, and recrystallize with methanol to obtain 5.89g of light yellow crystals, the yield 75.1%. 1 H NMR (CDCl 3 , 300 MHz) δ: 9.87 (s, 1H), 7,63 (m, 1H), 7.37 (dd, 1H), 7.34 (dd, 1H), 3.89 (s, 3H), 3.16 (s, 2H); ESI-MS m / z 238.1 [M+H] + .

Embodiment 2

[0068] Example 2. 3-methoxy-4-(4-carboxypropionyloxy)benzaldehyde

[0069]

[0070] Dissolve 5 g of vanillin in 50 mL of dichloromethane, add 4 g of succinic anhydride and a catalytic amount of DMAP, stir at room temperature for 36 hours, then add 100 mL of dichloromethane, wash the organic layer three times with saturated saline, and dry over anhydrous sodium sulfate. The organic layer was spin-dried, and recrystallized from methanol to obtain 5.77 g of light yellow crystals, with a yield of 69.6%. 1 H NMR (CDCl 3 , 300 MHz) δ: 9.89 (s, 1H), 7,62 (m, 1H), 7.39 (dd, 1H), 7.33 (dd, 1H), 3.87 (s, 3H), 3.26 (t, 2H), 3.15 (t, 2H); ESI-MS m / z 253.2 [M+H] + .

Embodiment 3

[0071] Example 3. 4-(4-formyl-2-methoxyphenoxy)butanoic acid

[0072]

[0073] Dissolve 3g of vanillin in 30mL of anhydrous acetone, add 5g of anhydrous potassium carbonate, slowly add 3.85g of ethyl bromobutyrate dropwise at room temperature, then overnight at room temperature, filter, spin dry acetone, add 30mL of methanol to dissolve, add 10% Sodium hydroxide solution 20mL, hydrolyzed overnight, adding 10% hydrochloric acid to adjust the pH to acidic, extracted with dichloromethane, combined the organic layer, dried over anhydrous sodium sulfate, spin-dried the organic layer, recrystallized from methanol to obtain 2.11g of a light yellow solid, the yield 45%. 1 H NMR (CDCl 3 , 300 MHz) δ: 9.84 (s, 1H), 7.72 (m, 1H), 7.51 (dd, 1H), 7.39 (dd, 1H), 3.92 (t, 2H), 3.88 (s, 3H), 2.26 ( t, 2H), 2.03 (m, 2H); ESI-MS m / z 238.4 [M+H] + .

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PUM

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Abstract

The invention provides a water-soluble monodemethoxycurcumin derivative as shown in general formula I and a pharmaceutically acceptable salt thereof. The compound has higher water solubility as well as high antitumor activity, has a function of inhibiting human gastric carcinoma cells MGC-803, human hepatocellular carcinoma cells Bel-7402, human chronic leukemia granulocytes K562 and human glioma U87 to different extents, and can be used for preparing an antitumor medicament, and the IC50 (Inhibitory Concentration 50) reaches the level of 1 [mu]M.

Description

technical field [0001] The invention relates to the technical field of new drug research and development, in particular to a novel water-soluble derivative of monodemethoxycurcumin and its preparation method and application. Background technique [0002] Curcumin is a phenolic pigment extracted and isolated from the plant turmeric root. It has a wide range of pharmacological activities, mainly including anti-inflammatory, anti-oxidation, anti-aging, anti-infection, lowering blood lipids, and anti-atherogenic Sclerosis and anti-tumor and other pharmacological activities. Curcumin is soluble in methanol, ethanol, propylene glycol; slightly soluble in water. It has the advantages of wide anti-cancer spectrum and low toxicity and side effects, but its clinical application is seriously affected by its shortcomings such as poor water solubility, instability under neutral and alkaline conditions, and low bioavailability. [0003] Also present in turmeric root are two analogues of...

Claims

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Application Information

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IPC IPC(8): C07C69/38C07C67/08C07C59/70C07C59/68C07C27/02C07C51/41A61K31/225A61K31/192A61P35/00A61P35/02
CPCC07C51/367C07C51/41C07C67/08C07C69/38C07C59/68C07C59/70
Inventor 石磊王之敏徐盛涛
Owner 石磊
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