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Resveratrol derivative and medical application thereof

A pharmacy and drug technology, applied in the field of resveratrol derivatives and their medical applications, can solve the problems of low oral bioavailability, biological activity to be improved, and poor water solubility of resveratrol

Inactive Publication Date: 2011-05-04
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, resveratrol has poor water solubility and low oral bioavailability, and its biological activity needs to be improved

Method used

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  • Resveratrol derivative and medical application thereof
  • Resveratrol derivative and medical application thereof
  • Resveratrol derivative and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Example 1 3,5-dimethoxy-4'-(1-methyl-1-ethoxycarbonylethoxy)stilbene (I 1 )Synthesis

[0087] Add 10g resveratrol (43.8mmol), 18.3g K 2 CO 3 (131.4mmol), 100mL dry DMF, stirred and heated to 55°C under the protection of nitrogen, added 12.8mL (87.6mmol) of ethyl 2-bromoisobutyrate dropwise, after the addition was completed, continued heating reaction at 55°C for 16h, and stopped heating. After cooling, 100 mL of ethyl acetate was added to the reaction solution; the resulting solution was washed 3 times with 1N hydrochloric acid, 50 mL each time; then the organic layer was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and separate the residue by column chromatography with 200-300 mesh silica gel, and elute with a mixed solvent of dichloromethane: ethyl acetate: acetic acid (9.5: 0.5: 0.2) to obtain 4'-(1-methanol (1-ethoxycarbonylethoxy)stilbene as a white solid, yield 78%.

[0088] Dissolve 1.2 g of 4′-(1-methyl-1-ethoxycarbonylethoxy) stilbene in 20 ...

Embodiment 2

[0089] Example 2 3,5-dimethoxy-4'-(1-methyl-1-carboxyethoxy)stilbene (I 2 )Synthesis

[0090] Will I 1 0.39g (1.06mmol) was dissolved in 20mL of MeOH / H 2 O (1:1), add 0.46g of K 2 CO 3 (3.36mmol), heat to reflux for 12h, stop heating, after cooling, add 40mL of water, adjust the pH to 3-4 with hydrochloric acid; then extract 3 times with ethyl acetate (20mL / time), combine the extracts, wash with water until Neutral, anhydrous Na for organic layer 2 SO 4 Dry, filter, concentrate and separate by column chromatography with 200-300 mesh silica gel, and elute with a mixed solvent of dichloromethane: ethyl acetate: acetic acid (7:3:0.08) to obtain the target compound I 2 , yield 89%. 1 H-NMR (d 6 -DMSO): δppm 1.10-1.12 (6H, s), 3.77 (6H, s), 6.38-6.39 (1H, m), 6.73-6.74 (2H, br.s), 6.92-6.94 (2H, d, J = 8.8Hz), 6.99-7.03 (1H, d, J = 16.4Hz), 7.18-7.22 (1H, d, J = 16.8Hz), 7.50-7.52 (2H, d, J = 8.8Hz).

[0091] Using conventional reaction conditions, the target compound I...

Embodiment 3

[0092] Example 3 3-(1-methyl-1-ethoxycarbonylethoxy)-4'-methoxystilbene (I 3 ) and 3,5-bis(1-methyl-1-ethoxycarbonylethoxy)-4'-methoxystilbene (I 4 )Synthesis

[0093] Dissolve resveratrol 10g (43.8mmol) in 200mL acetone, add 15.13g of K 2 CO 3(109.5mmol), 3.33mL of CH 3 I (65.7mmol), heated under the protection of nitrogen for reflux reaction for 10h, stop heating, after cooling, filter, wash the filter cake with acetone, combine the filtrate and lotion, concentrate and separate through column chromatography with 200-300 mesh silica gel, and use petroleum Ether: ethyl acetate: acetic acid (8.5: 1.5: 0.16) mixed solvent was eluted to obtain 8.9g 4'-methoxystilbene (II 1 ) and 2.5g 3,4'-dimethoxystilbene (II 2 ). II 1 H NMR spectrum ( 1 H-NMR (d 6 -DMSO) data are as follows: δppm 3.76 (3H, s), 6.13 (1H, br.s), 6.39 (2H, br.s), 6.80 (2H, d, J=8.8Hz), 6.90 (1H, d, J = 16.4Hz), 6.97 (1H, d, J = 16.4Hz), 7.48 (2H, d, J = 8.8Hz), 9.24 (2H, s). II 2 H NMR spectrum ( 1 ...

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Abstract

The invention relates to a resveratrol derivative and a medical application thereof, and in particular discloses a compound in a formula I as shown in the specification or pharmaceutically acceptable salt, ester, solvate and stereoisomer thereof, wherein R1, R2 and R3 are respectively independently selected from hydrogen atom, C1-C3 alkyl groups, or a substituent group in a formula i as shown in the specification, at least one of R1, R2 and R3 is selected from the C1-C3 alkyl groups, and simultaneously at least one of R1, R2 and R3 is selected from the substituent group in the formula i; R is selected from hydrogen atom, substituted or unsubstituted C1-C5 alkyl groups, substituted or unsubstituted C3-C6 naphthenic groups, benzyl groups or phenyl groups; and R4 and R5 are respectively independently selected from hydrogen atom, substituted or unsubstituted C1-C5 alkyl groups, or substituted or unsubstituted C3-C6 naphthenic groups. The invention also discloses a pharmaceutical composition containing the compound in the formula I, and the application of the compound in the formula I in preparing medicines for treating and / or preventing cardiovascular and cerebrovascular diseases. The compound in the formula I provided by the invention can be effectively used for treating and / or preventing the cardiovascular and cerebrovascular diseases such as hyperlipidaemia.

Description

technical field [0001] The present invention relates to novel resveratrol derivatives or pharmaceutically acceptable salts thereof, pharmaceutical compositions containing these compounds as active ingredients, and the use of said derivatives or pharmaceutically acceptable salts for the preparation of lipid-lowering drugs the use of. Background technique [0002] Cardiovascular and cerebrovascular diseases are the number one disease that threatens human life and health, and hypercholesterolemia characterized by elevated levels of plasma low-density lipoprotein and very low-density lipoprotein is one of the main pathogenic factors of cardiovascular and cerebrovascular diseases; blood lipids Elevation can also lead to fatty liver and cirrhosis. Blood lipid lowering therapy has become an important means to prevent and treat coronary heart disease and other cardiovascular and cerebrovascular diseases, and it is also an effective measure to treat fatty liver, liver fibrosis and l...

Claims

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Application Information

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IPC IPC(8): C07C69/708C07C59/68C07C67/31C07C27/02A61K31/216A61K31/192A61P9/00A61P3/06A61P39/06A61P7/02A61P9/08
Inventor 仲伯华李伟何新华贾红心
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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