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Synthesis and application of bornyl ferulate

A technology of bornyl ferulic acid and ferulic acid, which is applied in the field of chemical medicine, can solve the problems of fast metabolism, strong hydrophilicity, and poor fat solubility, and achieve good fat solubility, easy synthesis process, and high synthesis process. The effect of control

Active Publication Date: 2015-08-26
SUZHOU PHARMAVAN CANCER RES CENT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, ferulic acid molecule has strong hydrophilicity, poor fat solubility, fast metabolism in the body, less distribution in the brain, and it is difficult to play a role through the blood-brain barrier, which limits its application in the field of treatment of cerebrovascular diseases. The current clinical application of the drug Sodium Ferulate Injection mainly focuses on the treatment of cardiovascular diseases

Method used

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  • Synthesis and application of bornyl ferulate
  • Synthesis and application of bornyl ferulate
  • Synthesis and application of bornyl ferulate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] A synthetic route and specific synthetic method of D-bornyl ferulate are disclosed in this example, wherein the synthetic route is:

[0042]

[0043] Among them, 1a is dextroborneol, 2 is ferulic acid protected by phenolic hydroxyl group, R is a protecting group, and the ferulic acid protected by phenolic hydroxyl is condensed with dextroborneol under the catalysis of a condensation agent to obtain dextrorotary ferulic acid protected by phenolic hydroxyl group. Bornyl ester 3a, and then deprotected to obtain D-bornyl ferulic acid; the above-mentioned protecting group includes any one of the following: methyl, tert-butyl, triphenylmethyl, methoxymethyl, trimethyl silyl, tert-butyldimethylsilyl, benzyl and tetrahydropyranyl; the above-mentioned condensing agents include: dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-(3-di Methylaminopropyl)-3-ethylcarbodiimide, 4-dimethylaminopyridine, 1-hydroxybenzotriazole and 4-pyrrolidinylpyridine.

[0044] The synthetic me...

Embodiment 4

[0051] This embodiment discloses a synthetic route of L-bornyl ferulate, and the route is as follows:

[0052]

[0053] Among them, 1b is L-borneol, ferulic acid protected by phenolic hydroxyl group is condensed with L-borneol under the catalysis of a condensing agent to obtain L-bornyl ferulic acid ester 3b protected by phenolic hydroxyl group, and then deprotected to obtain L-bornyl ferulic acid ester.

[0054] The above-mentioned protecting groups include any one of the following: methyl, tert-butyl, triphenylmethyl, methoxymethyl, trimethylsilyl, tert-butyldimethylsilyl, benzyl and tetra Hydropyranyl; Ferulic acid protected by phenolic hydroxyl is condensed with L-borneol under the catalysis of a condensing agent to obtain L-bornyl ferulic acid protected by phenolic hydroxyl, and then deprotected to obtain L-bornyl ferulic acid.

[0055] Specific synthesis method:

[0056] A. Put 4-benzylferulic acid (7.5g, 0.026mol) into dichloromethane (50ml), cool down to 0°C in an ...

Embodiment 5

[0060] A synthetic route of D-bornyl ferulate is disclosed in this example:

[0061]

[0062] Haloacetyl D-bornyl ester 4a is reacted with organophosphorus reagent to obtain wittig phosphorus reagent 5a, and then wittig phosphorus reagent 5a is reacted with 3-methoxy-4 hydroxybenzaldehyde 6 under the action of alkali to obtain ferulic acid dextrose Sporbornyl ester.

[0063] Wherein, X is Cl, Br or I, R is PPh 3 X, P(O)Ph 2 or P(O)(OEt) 2 .

[0064] Organophosphorus reagents include: triphenylphosphine, ethoxydiphenylphosphine and triethyl phosphite; the base includes: lithium aluminum hydride, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydride, hydrogen Sodium Oxide, Potassium Hydroxide, Lithium Hydroxide and Potassium Carbonate.

[0065] The concrete method step of above-mentioned synthetic route is:

[0066] Step 1: Add chloroacetyl D-bornyl ester 4a (21.5g, 93.2mmol), triphenylphosphine (48.9g, 186mmol), and toluene (215ml) into the reactio...

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Abstract

The invention discloses bornyl ferulate. The bornyl ferulate and a pharmaceutically acceptable prodrug are applied to pharmacy; the bornyl ferulate is applied to treatment of cerebrovascular diseases; the bornyl ferulate comprises two structures including dextral bornyl ferulate and levorotatory bornyl ferulate; the structure formula of the dextral bornyl ferulate is shown as the specification; the structure formula of the levorotatory bornyl ferulate is shown as the specification; the dextral bornyl ferulate is an enantiomer of the levorotatory bornyl ferulate. A synthesis process of the bornyl ferulate is simple and short; raw materials are easy to obtain and are toxin-free and harmless; the synthesis process is easy to control; no harmful products are generated; the synthesis process is an environment-friendly and economical process and can be widely applied to the production of medicines for treating the cerebrovascular diseases.

Description

technical field [0001] The invention belongs to the field of chemical medicine, and in particular relates to the synthesis and application of D-(L-)bornyl ferulic acid. Background technique [0002] Ferulic acid (4-hydroxy-3-methoxycinnamic acid), originally found in the seeds and leaves of the plant, is a phenolic acid extracted from plants such as Angelica, Chuanqiong, and Ferula, which has anti-inflammatory properties , anti-oxidation, anti-thrombotic and a variety of physiological activities, widely used in health care products, cosmetics, medicine, pesticides and food additives and other fields. [0003] After research, it was found that ferulic acid can inhibit the aggregation and release of platelets, can significantly inhibit the formation of experimental thrombus, regulate the body's immunity, clear and inhibit free radical reactions, and ferulic acid molecules can affect the structure and structure of biological macromolecules in the body through various ways. The...

Claims

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Application Information

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IPC IPC(8): A61K31/216A61P9/10C07C69/734C07C67/343
CPCA61K31/216C07C67/343C07C69/734Y02P20/55
Inventor 李云森陈子珺邓世平刘乾高原冯海梅李勇
Owner SUZHOU PHARMAVAN CANCER RES CENT CO LTD
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