Use of dammarane-type triterpene derivatives

A technology of use and alkyl, applied in the field of use of dammarane-type triterpenoid derivatives, can solve the problem of less AMPK direct agonists and the like

Inactive Publication Date: 2015-05-06
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are very few research reports on AMPK direct agonists

Method used

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  • Use of dammarane-type triterpene derivatives
  • Use of dammarane-type triterpene derivatives
  • Use of dammarane-type triterpene derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The preparation of embodiment 1 compound 1

[0050]

[0051] In a 2L three-necked reaction flask, add 100g of American ginseng total saponins (purchased from Fusong Nature Bioengineering Co., Ltd.) and 1300ml of n-butanol, and stir for 10 minutes, then add 40g of sodium metal in batches, stir until no hydrogen is released, and then add 10 g of benzoyl peroxide was fed into oxygen, and heated to 120° C. for 24 hours. After the TLC detection reaction was complete, the reaction solution was cooled to room temperature, and n-butanol was removed under reduced pressure, dissolved in water, then extracted with petroleum ether and ethyl acetate in sequence, and the ethyl acetate part was distilled under reduced pressure to obtain an extract containing compound 1 , after silica gel column chromatography (petroleum ether: ethyl acetate = 2:1 (volume ratio) elution), compound 1 (7g, 7%) was obtained. 1 H NMR (300MHz, CDCl 3 )δ5.19(t,J=7.3Hz,1H),3.63(td,J=10.4,5.1Hz,1H),3.22(d...

Embodiment 2

[0052] The preparation of embodiment 2 compound 2

[0053]

[0054] In a 50ml three-neck reaction flask, dissolve compound 1 (200mg, 0.435mmol) in 15ml CH 2 Cl 2 After stirring for 10 min at -78°C, O 3 Reaction 2min. Then warm up to -3°C, add methylamine (0.1ml), NaBH(OAc) 3 (368.8mg, 1.7mmol) and CH 3 OH (8ml), stir overnight, after the reaction is complete, add 15ml of water, 2 Cl 2 (30ml) extracted twice, dried over anhydrous sodium sulfate, concentrated CH under reduced pressure 2 Cl 2 , Compound 2 was obtained by silica gel column chromatography (dichloromethane / methanol / triethylamine, 40:1:0.5 (volume ratio)), with a yield of 85%. 1 H NMR (300MHz, CDCl 3 )δ4.12(m,1H),3.52(td,J=13.0,6.2Hz,1H),3.21(dd,J=10.9,5.0Hz,1H),2.94(m,1H),2.62(m,1H ),2.47(s,3H),1.13(s,3H),0.99(s,3H),0.98(s,3H),0.88(s,6H),0.78(s,3H),0.73(d,J= 11.0Hz,1H);ESI-MS450.7[M+H] + .

Embodiment 3

[0055] The preparation of embodiment 3 compound 3

[0056]

[0057] Except replacing methylamine with ethylamine, compound 3 is prepared in the same manner as in Example 2; Silica gel column chromatography (dichloromethane / methanol / triethylamine, 45:1:0.5 (volume ratio)), the yield is 86%. 1 H NMR (300MHz, CDCl 3 )δ3.55(td,J=12.9,6.3Hz,1H),3.19(dd,J=10.9,4.9Hz,1H),2.93(m,1H),2.72(m,1H),2.58(m,1H ),2.48(m,1H),2.09(m,1H),1.15(s,3H),1.11(t,J=7.2Hz,3H),0.99(s,3H),0.98(s,3H),0.89 (s,3H),0.88(s,3H),0.78(s,3H),0.73(d,J=10.7Hz,1H);ESI-MS464.7[M+H] + .

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Abstract

The invention provides a use of dammarane-type triterpene derivatives represented by general formula I or pharmaceutically acceptable salts thereof, and a use of a medicinal composition containing the derivatives or the pharmaceutically acceptable salts thereof, and a plant extract product. The dammarane type triterpene derivatives, the medicinal composition and the plant extract product can activate AMPKalpha2beta1gamma1 at the molecular level, and can be used to prepare AMPK micromolecule activators in order to prepare medicines for preventing or treating AMPK related diseases.

Description

technical field [0001] The present invention relates to the use of dammarane-type triterpene derivatives, in particular to dammarane-type triterpene saponins, dammarane-type triterpene and derivatives modified with dammarane-type triterpene as the parent structure, including such The composition of derivatives and the use of plant extracts in the preparation of AMPK agonists, and the use in the preparation of medicines for treating or preventing diseases related to AMPK. Background technique [0002] At present, type II diabetes has become a major disease threatening human health, and its main pathogenesis is insulin resistance. Therefore, promoting glucose uptake and fatty acid oxidation through non-insulin-dependent mechanisms has become an important way to prevent and treat type II diabetes. In recent years, studies have found that AMP-activated protein kinase (AMPK) is an important Ser / ThrD protein kinase, which can sense the energy metabolism state of cells and the who...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/58A61K31/575A61K31/585A61K31/7034A61P3/10A61P3/06A61P3/04A61P5/50A61P9/04A61P9/06A61P9/10A61P11/00A61P11/06A61P9/12A61P1/16A61P13/08A61P1/18A61P13/12A61P19/02A61P29/00A61P35/00C07J17/00C07J43/00C07J41/00C07J9/00C07J19/00
Inventor 胡立宏李佳刘军华李静雅黄勇陈达锴许磊
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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