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Oridonin derivative, preparation method and uses thereof

A technology of oridonin A and its derivatives, which is applied in the field of natural medicine and medicinal chemistry, and can solve the problems of antitumor activity, insufficient water solubility, and limited use

Inactive Publication Date: 2008-03-12
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Summarizing the research results on the structural modification of oridonin so far, we found that all the reported oridonin and its derivatives have insufficient antitumor activity and water solubility, which limits their further development as new drugs

Method used

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  • Oridonin derivative, preparation method and uses thereof
  • Oridonin derivative, preparation method and uses thereof
  • Oridonin derivative, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0118] 7,14-Acetonid oridonine A

[0119] Dissolve oridonin (100mg, 0.274mmol) in 3ml of anhydrous acetone, add 0.4ml of 2,2-dimethoxypropane and a catalytic amount of p-toluenesulfonic acid, nitrogen protection, reflux reaction for 1h, cool to room temperature, add saturated NaHCO 3 solution with CHCl 3 Extracted 3 times, then backwashed 2 times with water, the organic layer was washed with anhydrous MgSO 4 Drying, evaporation to dryness, column chromatography (petroleum ether: acetone = 3:1 ~ 1:1), yielded 94.1 mg of white solid, yield: 85%, m.p.219-221°C.

[0120] MS-ESI (m / z): 427[M+Na] + , 405[M+1] + , 403[M-1] - .

Embodiment 2

[0122] 1-O-acetyl-7,14-acetonid oridonin

[0123] Dissolve the compound (80 mg, 0.20 mmol) prepared in Example 1 in 2 ml of pyridine, add 0.3 ml of acetic anhydride, stir at room temperature for 14 h, add saturated NaHCO 3 The solution was stirred until no bubbles were produced, extracted 3 times with ethyl acetate, the organic layer was washed 4 times with water, and anhydrous MgSO 4 Dry overnight and evaporate to dryness under reduced pressure. used directly in the next reaction.

[0124] MS-ESI(m / z): 469[M+Na] + , 447[M+1] + .

Embodiment 3

[0126] 1-O-acetyl oridonin A

[0127] The compound (80 mg, 0.2 mmol) prepared in Example 2 was dissolved in 2 ml of 80% acetic acid solution, stirred at room temperature for 10 h, evaporated to dryness under reduced pressure (adding toluene to bring out acetic acid and water), the reaction was carried out quantitatively, and the obtained crude product was subjected to Purified by column chromatography (petroleum ether: acetone = 2:1) to obtain 63.7 mg of white solid, yield: 78.5%. m.p.196-198°C.

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Abstract

The present invention relates to a natural drug and the chemical field of drugs, specifically relating to an oridonin derivative (I); the derivative is the product after the structural transformation of C1 and C14 of the oridonin. The present invention also discloses the preparation method of the oridonin derivatives and the application of the novel oridonin derivative in the anti-tumor field.

Description

technical field [0001] The present invention relates to the fields of natural medicine and medicinal chemistry, in particular to a class of oridonin A derivatives, which are products obtained by structural modification of the C1 and C14 positions of oridonin A. The invention also discloses the preparation method of these oridonin A derivatives and the anti-tumor application of these novel derivatives. Background technique [0002] Oridonin is a natural organic compound of ent-kaurene diterpenoid isolated from Rabdosia plants, and it is the main active ingredient of Oridonin. Clearing heat and detoxifying, promoting blood circulation and removing blood stasis, antibacterial and anti-inflammatory, anti-tumor and other effects. Studies have found that Rubescensine A has definite anti-tumor activity in vivo and in vitro, and its anti-tumor spectrum is also broad. Rat Ehrlich ascites carcinoma, ascites type and solid type of liver cancer, and sarcoma S180 all have anti-tumor ef...

Claims

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Application Information

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IPC IPC(8): C07D493/08A61K31/352A61P35/00
Inventor 徐进宜吴晓明杨静怡冉倩王磊王致轩袁胜涛张陆勇沈明勤
Owner CHINA PHARM UNIV
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