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Zedoary turmeric lactone enantiomer and preparation method thereof

A technology of enantiomer and curcumolactone, which is applied in the field of enantiomer of curcumolactone and its preparation, to achieve good anti-tumor activity

Inactive Publication Date: 2013-08-07
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A total synthesis method of 4,7-epimer (-)-Curdione (Ⅱ) of curdione has been reported in the literature, which is obtained by 12 steps of reaction with (-)-carvone as raw material, and the total yield is At 2.54%, not only the steps are cumbersome, but also the yield is low (Zhao, R. B. et al., 1988)

Method used

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  • Zedoary turmeric lactone enantiomer and preparation method thereof
  • Zedoary turmeric lactone enantiomer and preparation method thereof
  • Zedoary turmeric lactone enantiomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1. Preparation of 8-OH-Neocrudione (Ⅵ)

[0039] Add Neocurdione 500mg (2.12mmol) to a 50ml round-bottomed flask with a stirring bar, dissolve it in 6ml of methanol, and add NaBH in batches under ice-cooling 4 100mg (2.64mmol), stirred reaction at 0°C. After reacting for 4.5 hours, the reaction solution was evaporated to dryness, 3ml of water was added, adjusted to neutrality with 1N HCl, extracted three times with an equal volume of ethyl acetate, and the ester layer was evaporated to dryness to obtain oily product VI. It does not need to be purified and can be directly used for the next reaction.

[0040] 2. 8-OH-4- epi - Preparation of neocurdione (VII)

[0041] with CaCl 2Add dry oily product VI to a 50ml round bottom flask with a drying tube, a spherical condenser, and a stirring bar, dissolve it in 10ml of anhydrous benzene, add 60mg (0.53mmol) of potassium tert-butoxide, and reflux at 83°C for 6h until the reaction reaches equilibrium . The product was sep...

Embodiment 2

[0047] 1. Preparation of 8-OH-Neocrudione (Ⅵ)

[0048] Add Neocurdione 500mg (2.12mmol) to a 50ml round bottom flask with a stirring bar, dissolve it in 15ml methanol, add NaBH in batches under ice-cooling 4 100mg (2.64mmol), heated to 50°C and stirred to react. After reacting for 2 hours, the reaction solution was evaporated to dryness, 3ml of water was added, adjusted to neutrality with 1N HCl, extracted three times with an equal volume of ethyl acetate, and the ester layer was evaporated to dryness to obtain oily product VI. It does not need to be purified and can be directly used for the next reaction.

[0049] 2. 8-OH-4- epi - Preparation of neocurdione (VII)

[0050] with CaCl 2 Add dry oily product VI to a 50ml round bottom flask with a drying tube, a spherical condenser, and a stirrer, dissolve it in 10ml of anhydrous benzene, add 60mg (0.53mmol) of potassium tert-butoxide, and react at room temperature for 6h until the reaction reaches equilibrium. The product ...

Embodiment 3

[0052] Preparation of (-)-Curdione (Ⅱ)

[0053] Synthesize compound VII8-OH-4- with the method in embodiment 1 or 2 epi -neocurdione, add 72.3mg (0.30mmol) of compound VII to a 50ml round bottom flask with a stirring bar, add 5ml of dichloromethane as a solvent, add 225.7mg (0.6mmol) of PDC, and stir the reaction at room temperature for 2h. Add 0.5 g of silica gel to the reaction solution, continue stirring for 0.5 h, filter, and evaporate to dryness to obtain 69.5 g of white solid II, with a yield of 96%.

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Abstract

The invention belongs to the technical field of medicine, and relates to a preparation method for a zedoary turmeric lactone enantiomer having anti-tumor activity. The structure of the zedoary turmeric lactone enantiomer is represented by a structure (I). The preparation method comprises: adopting new curdione separated from zedoary turmeric oil as a substrate, carrying out a three-step chemical reaction to carry out isomerization on chiral carbon on site 4 to obtain a curdione enantiomer, and carrying out acid catalysis. The test results show that the prepared enantiomer has good anti-tumor activity.

Description

technical field [0001] The invention relates to an enantiomer of curcumolactone with antitumor activity and a preparation method thereof, and relates to the chiral modification of a class of sesquiterpenoids. Background technique [0002] The traditional Chinese medicine Zezhu is a plant of the Zingiberaceae Curcuma Curcuma phaeocaulis Val.), Guangxi Curcuma ( Curcuma kwangsiensis S. G. Lee et C. F. Liang) and Wen Yujin ( Curcuma wenyujin Y H. Chen et C. ling) dry rhizome. Zedoary oil is the volatile oil component extracted from the traditional Chinese medicine Zedoary. Zedoary oil has anti-tumor (Sun et al., 2009; Wu et al., 2000), anti-oxidation (Loc et al., 2008; Mau et al., 2003 ), antibacterial (Lai et al.,2004; Wilson et al., 2005) and other pharmacological effects. Curdione (compound Ⅲ) is one of the main active components isolated from zedoary oil, with an optical rotation of +263.3°. Studies have found that curcumadione has a variety of pharmacological a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/94A61K31/365A61P35/00
Inventor 游松金旦妮秦斌张新张朗梁萍穆矛刘冰滢王潇莹马国振
Owner SHENYANG PHARMA UNIVERSITY
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