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Caffeic acid diester compounds and prepartion method thereof, and application of preparing medicine for curing thrombus

A caffeic acid and compound technology, which is applied in the preparation of organic compounds, the preparation of carboxylic acid esters, chemical instruments and methods, etc., can solve the problem that acetylsalicylic acid has large adverse reactions, can not exert good efficacy, and has low bioavailability. To achieve the effect of strong antithrombotic pharmacological effect, reduced clinical dosage, and high bioavailability

Inactive Publication Date: 2009-11-25
NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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Problems solved by technology

[0002] Caffeic acid is an important natural product, which exists in a variety of traditional Chinese medicine plants. Recent studies have shown that caffeic acid extracted from honeysuckle water extraction and alcohol precipitation has a strong anti-ADP-induced platelet aggregation in vitro, and has the ability to inhibit The role of thrombosis, in addition, it has been reported that caffeic acid has the functions of regulating the body's immune function, scavenging and inhibiting free radicals, etc. It is an important natural antioxidant, and studies have shown that caffeic acid derivatives, such as: caffeic acid ethyl ester has Strong anti-inflammatory effect, because there are three hydroxyl groups in the caffeic acid molecule, the polarity is relatively high, the bioavailability of the caffeic acid is low after the human body takes it, and the drug effect cannot be exerted well
Clinically, acetylsalicylic acid has a certain antithrombotic effect, but the adverse reactions of acetylsalicylic acid are relatively large. After the human body takes a large dose of acetylsalicylic acid, adverse reactions such as gastrointestinal bleeding occur

Method used

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  • Caffeic acid diester compounds and prepartion method thereof, and application of preparing medicine for curing thrombus
  • Caffeic acid diester compounds and prepartion method thereof, and application of preparing medicine for curing thrombus
  • Caffeic acid diester compounds and prepartion method thereof, and application of preparing medicine for curing thrombus

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1 The preparation of methyl-3-(3,4-(2-acetoxy-benzoyloxy)phenyl)-acrylate

[0038] (1) Preparation of methyl caffeate

[0039] Caffeic acid (0.9 g, 5 mmol) was completely dissolved in methanol (10 ml), then concentrated sulfuric acid (0.067 ml, 1.25 mmol) was added, and the reaction was carried out in a microwave reactor with the temperature set at 100 ° C and the pressure set at 180 PSI , power set at 200W, microwave reaction for 4 minutes, cooling, adjust the pH value to neutral with saturated sodium carbonate aqueous solution, then extract with ethyl acetate, then wash with water and saturated brine successively, and finally obtain the purified product with n-hexane After recrystallization, 0.91 g of a colorless solid was obtained, with a yield of 94%. get the product 1 H NMR (300MHz, DMSO-d 6 )δ3.69(s, 3H), 6.27(d, J=15.9Hz, 1H), 6.76(d, J=8.0Hz, 1H), 7.00(dd, J 1 =2.0Hz,J 2 =8.0Hz, 1H), 7.05(d, J=2.0Hz, 1H), 7.48(d, J=15.9Hz, 1H), 9.13(s, 1H), 9.57(...

Embodiment 2

[0042] Embodiment 2 Preparation of ethyl-3-(3,4-(2-acetoxy-benzoyloxy)phenyl)-acrylate

[0043] (1) Preparation of ethyl caffeate

[0044] Caffeic acid (0.9 g, 5 mmol) was completely dissolved in absolute ethanol (10 ml), then added concentrated sulfuric acid (0.067 ml, 1.25 mmol), placed in a microwave reactor for reaction, the temperature was set at 100 ° C, the pressure was set Set at 180PSI, power at 200W, microwave reaction for 4 minutes, cool down, adjust the pH value to neutral with saturated sodium carbonate aqueous solution, then extract with ethyl acetate, then wash with water and saturated saline in sequence, and finally obtain the purified product with Recrystallized from n-hexane to obtain 0.97 g of a colorless solid with a yield of 93%. product of 1 H NMR (300MHz, DMSO-d 6 )δ1.24(t, 3H), 4.15(q, 2H), 6.25(d, J=15.9Hz, 1H), 6.76(d, J=8.2Hz, 1H), 7.01(m, 2H), 7.47( d, J=15.9Hz, 1H), 9.31(b, 2H); ESI-MS m / z: 209[M+H] + (100), indicating that the product was eth...

Embodiment 3

[0047] Example 3 Preparation of n-propyl-3-(3,4-(2-acetoxy-benzoyloxy)phenyl)-acrylate

[0048] (1) Preparation of Propyl Caffeate

[0049] Caffeic acid (0.9 g, 5 mmol) was completely dissolved in n-propanol (10 ml), then added concentrated sulfuric acid (0.067 ml, 1.25 mmol), placed in a microwave reactor for reaction, the temperature was set at 100 ° C, the pressure was set Set at 180PSI, power at 200W, microwave reaction for 5 minutes, cool down, adjust the pH value to neutral with saturated sodium carbonate aqueous solution, then extract with ethyl acetate, then wash with water and saturated saline in sequence, and finally obtain the purified product with After recrystallization from n-hexane, 1.03 g of a colorless solid was obtained, with a yield of 93%. That 1 H NMR (300MHz, DMSO-d 6 )δ0.92(t, 3H), 1.64(q, 2H), 4.07(t, 2H), 6.26(d, J=15.9Hz, 1H), 6.75(d, J=8.0Hz, 1H), 7.02( m, 2H), 7.47(d, J=15.9Hz, 1H), 9.11(s, 1H), 9.56(s, 1H); ESI-MS m / z: 223[M+H] + (100), indica...

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Abstract

The invention discloses caffeic acid diester compounds of formula (I) and prepartion method thereof, and application of preparing medicine for curing thrombus, experments show that the invention synthesized caffeic acid diester compounds has strong inhibition function to platelet aggregation induced by ADP, comparison of 50% aggregation inhibition concentration shows that, the invention provided caffeic acid diester compounds has better inhibition function to platelet aggregation than caffeic acid and acetylsalicylic acid, the caffeic acid diester compounds obtained by condensation of caffeic acid and acetylsalicylic acid has synergistic function with less clinical dosage, reduced untoward effect. The invention provided method for preparing caffeic acid diester compounds uses microwave reaction that reduces reaction time and improves reaction efficiency, and the cost is reduced, the invention also has excellent operability and certain protection function to environment.

Description

technical field [0001] The invention relates to a compound, in particular to a caffeic acid diester compound synthesized by taking caffeic acid as a core through structural modification, and also relates to a preparation method and application of the caffeic acid diester compound. Background technique [0002] Caffeic acid is an important natural product, which exists in a variety of traditional Chinese medicine plants. Recent studies have shown that caffeic acid extracted from honeysuckle water extraction and alcohol precipitation has a strong anti-ADP-induced platelet aggregation in vitro, and has the ability to inhibit The role of thrombosis, in addition, it has been reported that caffeic acid has the functions of regulating the body's immune function, scavenging and inhibiting free radicals, etc. It is an important natural antioxidant, and studies have shown that caffeic acid derivatives, such as: caffeic acid ethyl ester has Strong anti-inflammatory effect, because ther...

Claims

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Application Information

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IPC IPC(8): C07C69/90C07C67/08A61K31/621A61P7/02
Inventor 唐于平李念光段金廒
Owner NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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