Ursolic acid-glycolysis inhibitor DCA conjugate and application thereof

A technology of ursolic acid and its application, which is applied in the field of ursolic acid derivatives and its application, can solve the problems of low bioavailability, and achieve the effect of excellent proliferation inhibition and reduced content

Inactive Publication Date: 2015-10-21
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through the covalent coupling of DCA with good bioavailability and ursolic acid with poor water solubility, the physical and chemical properties of the compound are improved to solve the problem of low bioavailability of ursolic aci

Method used

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  • Ursolic acid-glycolysis inhibitor DCA conjugate and application thereof
  • Ursolic acid-glycolysis inhibitor DCA conjugate and application thereof
  • Ursolic acid-glycolysis inhibitor DCA conjugate and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of DCA-UA

[0026] At room temperature, dissolve 0.5 g UA in 20 mL 1v / 1v pyridine:dichloromethane mixed solution, add 0.1eq DMAP, and slowly add 108 μL dichloroacetyl chloride dropwise to the aforementioned solution under magnetic stirring conditions, and the dropwise addition is completed Then continue to stir for 8-10h. After the reaction was complete, dichloromethane was distilled off under reduced pressure. Add 100 mL of water to the reaction flask to precipitate the product, filter with suction, wash the filter cake with 500 mL of water until neutral, dry in vacuum, and obtain DCA-UA by column chromatography.

[0027] Properties: White powder; Yield: 70.51%

[0028] IR data: see 2

[0029] HRMS: Theoretical value: 565.2857 m / z Actual value: 565.2860 m / z

[0030] 1 H NMR (400 MHz, CDCl 3 ) δ 5.97 (d, J = 2.9 Hz, 1H), 5.26 (d, J = 2.2 Hz, 1H), 4.67 (dd, J = 20.3, 18.0 Hz, 1H), 2.40 – 2.15 (m, 1H), 2.09 – 1.84 (m, 4H), 1.74 (s, 6H), ...

Embodiment 2

[0031] Embodiment 2: the synthesis of DCA-UP

[0032] At room temperature, 0.5 g of DCA-UA was dissolved in 20 mL of dichloromethane. Under the condition of magnetic stirring, 0.6 mL of oxalyl chloride was slowly added dropwise to the above solution, and the stirring was continued for 8-10 h after the dropwise addition was completed. After the reaction was complete, the gas and solvent were distilled off under reduced pressure. Under magnetic stirring, the aforementioned product was dissolved in 20 mL of dichloromethane, and slowly added dropwise to a solution of 0.4 g of piperazine and 100 μL of triethylamine in 20 mL of dichloromethane. After the dropwise addition was completed, stirring was continued for 12h. After the reaction was complete, 20 mL of dichloromethane was added to the reaction flask, and the reaction system was extracted 2-4 times with 50 mL of 1N HCl solution until the pH was 3-4. The organic layer was collected by liquid separation, dried over anhydrous so...

Embodiment 3

[0037] Embodiment 3: the synthesis of DCA-UH

[0038] At room temperature, 0.5 g of DCA-UA was dissolved in 20 mL of dichloromethane. Under the condition of magnetic stirring, 0.6 mL of oxalyl chloride was slowly added dropwise to the above solution, and the stirring was continued for 8-10 h after the dropwise addition was completed. After the reaction was complete, the gas and solvent were distilled off under reduced pressure. Under magnetic stirring, the aforementioned product was dissolved in 20 mL of dichloromethane, and slowly added dropwise to a solution of 0.5 g of hexamethylenediamine and 100 μL of triethylamine in 20 mL of dichloromethane. After the dropwise addition was completed, stirring was continued for 12h. After the reaction was complete, 20 mL of dichloromethane was added to the reaction flask, and the reaction system was extracted 2-4 times with 50 mL of 1N HCl solution until the pH was 3-4. The organic layer was collected by liquid separation, dried over an...

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Abstract

The invention relates to an ursolic acid derivative and an application thereof, in particular to an ursolic acid derivative having the functions of tumor cell apoptosis resisting and metabolism double targeting and an application thereof. The ursolic acid derivative is formed after dichloroacetylation of the ursolic acid and the derivative of the ursolic acid. Formula I, formula II and formula III of the ursolic acid derivative are as shown in the specification. The invention further provides the application of the ursolic acid derivative to preparation of anti-tumor drugs.

Description

technical field [0001] The present invention relates to a derivative of ursolic acid and its application, in particular to a new type of ursolic acid and its derivatives formed after dichloroacetylation Functional ursolic acid derivatives and their applications. Background technique [0002] Natural products are increasingly becoming an important source of new anticancer drugs due to their structural diversity and low toxicity. Existing studies have shown that 70% of anticancer drugs are derived from natural resources. Therefore, extracting active ingredients from natural plants as a lead is an important method for designing and synthesizing new anticancer drugs. Ursolic acid (Ursolic Acid, referred to as UA), CAS number: 77-52-1, is a natural source of α-amyresin alcohol type pentacyclic triterpenoids. According to incomplete statistics, UA can be isolated from 108 species of plants in 34 families in nature, and it is mainly distributed in medicinal plants such as Ligust...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61K31/58A61P35/00
CPCC07J63/008
Inventor 邵敬伟杨祥郑清陈秀芬禹小波向利平
Owner FUZHOU UNIV
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