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Poly-carbonyl curcumin derivative containing carboxyl group, preparation method and application thereof

A technology of carbonyl curcumin and derivatives, applied in the field of medicine, can solve the problems of low bioavailability, low solubility, large dosage, etc., achieve the effect of inhibiting β-secretase, protecting nerve cells, and high stability

Active Publication Date: 2015-10-14
JIANGSU KANION PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, due to poor stability, low solubility, low in vivo bioavailability and large dosage of curcumin, the popularization and use of curcumin are limited.

Method used

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  • Poly-carbonyl curcumin derivative containing carboxyl group, preparation method and application thereof
  • Poly-carbonyl curcumin derivative containing carboxyl group, preparation method and application thereof
  • Poly-carbonyl curcumin derivative containing carboxyl group, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Dissolve acetylacetone (1g, 10mmol) and boron oxide (0.49g, 7mmol) in 10mL of ethyl acetate, stir at 40°C for 30min, then add vanillin (1.522g, 10mmol), p-formyl Methyl benzoate (1.642g, 10mmol) and tributyl borate (4.6g, 20mmol) were stirred for 30min. n-Butylamine (1mL) was dissolved in 10mL of ethyl acetate and added dropwise slowly for 30min. After the dropwise addition was completed, it was stirred at 40°C for 4h, and left overnight to make the reaction complete. The mixture was hydrolyzed with aqueous hydrochloric acid (0.4N, 15mL) at 60°C for 1 h, the aqueous phase was extracted three times with ethyl acetate, the organic phases were combined, washed with water until neutral, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and flash silica gel Column chromatography (petroleum ether: acetone = 2:1) gave an orange-yellow solid product, 532 mg, with a yield of 14%. That is the intermediate (Ⅱ).

[0039] (2) Dissolve i...

Embodiment 2

[0045] (1) Dissolve acetylacetone (1g, 10mmol) and boron oxide (1g,) in 10mL of ethyl acetate, stir at 40°C for 30min, then add vanillin (1.522g, 10mmol), p-formylbenzoic acid Methyl ester (1.642g, 10mmol) and tributyl borate (4.6g, 20mmol), continued stirring for 30min. n-Butylamine (1mL) was dissolved in 10mL of ethyl acetate and added dropwise slowly for 30min. After the dropwise addition was completed, it was stirred at 40°C for 4h, and left overnight to make the reaction complete. The mixture was hydrolyzed with aqueous hydrochloric acid (0.4N, 15mL) at 60°C for 1 h, the aqueous phase was extracted three times with ethyl acetate, the organic phases were combined, washed with water until neutral, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and flash silica gel Column chromatography (petroleum ether: acetone = 2:1) gave an orange-yellow solid product, which was intermediate (Ⅱ).

[0046] (2) Dissolve intermediate (II) (174mg, ...

Embodiment 3

[0047] Embodiment 3 The drug efficacy test of carboxy polycarbonyl curcumin derivatives of the present invention

[0048] Experiment 1: Activity screening of acetylcholinesterase inhibitors

[0049] 1. The purpose of the experiment: to accurately screen samples with acetylcholinesterase inhibitor activity.

[0050] 2. Experimental materials

[0051] 2.1 Drugs and experimental reagent consumables

[0052] Sample: carboxyl-containing polycarbonyl curcumin derivative (abbreviation: Jhs-A-5), prepared according to the method in Example 1.

[0053] Curcumin reference substance, Nanjing Zelang Pharmaceutical Technology Co., Ltd.

[0054] Acetylcholinesterase (Electric eel), sigma

[0055] Thioacetylcholine iodide, Sigma

[0056] 5,5-dithiobisnitrobenzoic acid (DTNB), sigma

[0057] Tacrine hydrochloride (Tacrine hydrochloride), sigma company

[0058] Disodium hydrogen phosphate, Shantou Xilong Chemical Factory Co., Ltd.

[0059] Sodium dihydrogen phosphate, Nanjing Chemical ...

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Abstract

The invention discloses a poly-carbonyl curcumin derivative containing carboxyl group, a preparation method and an application thereof. A structure of the poly-carbonyl curcumin derivative containing the carboxyl group is represented as the formula (I). The poly-carbonyl curcumin derivative containing the carboxyl group is high in stability and solubility, has the effects of inhibiting [beta]-secretase and acetylcholin esterase, resisting oxidization and protecting nerve cells, and can be used for preparing drugs for Alzheimer's disease.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a chemically synthesized new compound, its preparation method and application. Background technique [0002] In recent years, with the aging of society, senile dementia has become a major social and medical problem, so the drug for the treatment of senile dementia is in urgent need of development. [0003] Vascular dementia (VD), Alzheimer's disease (Alzheimer's disease, referred to as AD) is a symptom of Alzheimer's disease, is a primary degenerative brain degenerative disease of unknown etiology. Alzheimer's disease has no clear pathology so far, and various pathological hypotheses emerge in endlessly, such as: Aβ (Btea-Amyloid, β-amyloid protein) cascade hypothesis, cholinergic hypothesis, protein metabolism disorder, free radical theory, excitotoxicity, calcium Ions (Ca 2+ ) Disorders of homeostasis, secondary mutation hypothesis, etc. [0004] The main active ingredient ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C65/40C07C27/02A61K31/192A61P25/28
Inventor 萧伟王振中李兆亮孟兆青陶晓倩丁岗
Owner JIANGSU KANION PHARMA CO LTD
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