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2-substituted and/or 27-substituted betulinic acid derivatives as well as preparation method and applications thereof

A derivative, the technology of betulinic acid, applied in the field of betulinic acid derivatives and its preparation, can solve the problem of unsatisfactory transformation

Active Publication Date: 2016-08-17
四川梓橦宫药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] (2) The modification of the 19-position isopropenyl group of betulinic acid has not obtained very satisfactory results
Betulinic acid derivatives substituted in other positions have not been reported

Method used

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  • 2-substituted and/or 27-substituted betulinic acid derivatives as well as preparation method and applications thereof
  • 2-substituted and/or 27-substituted betulinic acid derivatives as well as preparation method and applications thereof
  • 2-substituted and/or 27-substituted betulinic acid derivatives as well as preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0069] The preparation method of the 2- and / or 27-substituted betulinic acid derivatives shown in formula I comprises the following steps:

[0070] a. Use 95%wt ethanol to leaching the fresh leaves of C. japonica for 2 to 4 times, each time for 24h, combine the leaching solution and filter, and obtain the extract after the filtrate is concentrated; then ultrasonically dissolve the extract in 20%wt ethanol aqueous solution , extracted with ethyl acetate;

[0071] b. After the extracted ethyl acetate layer is concentrated, the crude product is obtained after column chromatography; the column chromatography eluent is a mixed solution of petroleum ether and ethyl acetate, and its volume ratio is successively 20: 1, 15: 1 , 10: 1, 5: 1, 3: 1, 1: 1; the chromogenic agent of the column chromatography is 5% vanillin concentrated sulfuric acid;

[0072] c. The above crude product was heated and dissolved with 70% wt ethanol and DMF, and the insoluble matter was removed by filtration. ...

Embodiment 1

[0076] The preparation of embodiment 1 compound 1

[0077]

[0078] Weigh 4 kg of fresh leaves of C. japonica, cold-soak in 10 times the amount of 95% ethanol three times, each time for 24 hours, combine the leachate and filter, and concentrate the filtrate under reduced pressure to obtain an extract. Take 300g of extract and add 3L of 20% ethanol aqueous solution, ultrasonically dissolve, sequentially extract with petroleum ether (1×3L), ethyl acetate (3×6L), take water layer, petroleum ether layer, ethyl acetate layer respectively, put on The results of liquid phase detection showed that most of the target components entered the ethyl acetate layer, while there was no target component in the aqueous liquid, and a small amount of target components in the petroleum ether layer.

[0079]Concentrate the ethyl acetate layer until solid precipitates, pour it out while it is hot, stir evenly and add a small amount of ethyl acetate to dissolve until there are no solid particles, ...

Embodiment 2

[0083] The preparation of embodiment 2 compound 2 and compound 3

[0084]

[0085]

[0086] Compound 2 and Compound 3 were prepared in a similar manner to Compound 1.

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Abstract

The invention belongs to the field of medical medicines, and concretely relates to 2-substituted and / or 27-substituted betulinic acid derivatives as well as a preparation method and applications thereof. The structure of 2-substituted and / or 27-substituted betulinic acid derivatives is shown in a formula I. The invention also provides the preparation method and applications of the 2-substituted and / or 27-substituted betulinic acid derivatives. The 2-substituted and / or 27-substituted betulinic acid derivatives have good safety and clear efficacies for resisting cancer, resisting organ fibrosis, regulating immunity, resisting digestive tract inflammation and ulcer, resisting fungus and other respects, and other respects; and the derivatives provide new choices for preparing medicaments for treating the related diseases.

Description

technical field [0001] The invention belongs to the field of chemical medicine, and specifically relates to betulinic acid derivatives substituted at the 2-position and / or 27-position, a preparation method and application thereof. Background technique [0002] Betulinic acid (betulinic acid) is a lupin-type pentacyclic triterpenoid compound, which is widely distributed in various plants such as Rhamnaceae, Myrtaceae, and Betulaceae, but the content is generally low. Due to the large parent ring structure of betulinic acid, its molecular polarity is small and its fat solubility is high. Therefore, betulinic acid has low solubility in water and is easily soluble in ether, chloroform, ethanol and other organic solvents. Betulinic acid has strong selective cytotoxicity to melanoma cells (Pisha E, Chai H, Lee I S, et al. Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis[J].Nat Med , 1995,1(10):1046-1051); the apoptos...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61P31/10A61P35/00A61P37/02A61P1/00A61P29/00A61P1/04A61P1/16
Inventor 徐超群李东晓陈雏张毅阮佳詹雁谭镭袁志翔余悦白筱璐
Owner 四川梓橦宫药业股份有限公司
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