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Water soluble oridonin derivative and preparation method thereof

A water-soluble derivative technology, applied in the field of water-soluble oridonin derivatives and its preparation, can solve the problems of bitter taste, poor water solubility, limited application, etc.

Active Publication Date: 2009-09-09
SHENZHEN JYMED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Oridonin is a colorless prismatic crystal with a very bitter taste, insoluble in water, but soluble in organic solvents such as ether, methanol, ethanol, etc. The water solubility of oridonin is only 0.75mg / ml, and its water solubility is poor The nature of the drug greatly limits its application as a drug

Method used

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  • Water soluble oridonin derivative and preparation method thereof
  • Water soluble oridonin derivative and preparation method thereof
  • Water soluble oridonin derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The synthesis of the oridonine A of embodiment 1 propylidene protection

[0044] Under nitrogen protection, 10 mg p-toluenesulfonic acid was added to 0.3 g (0.823 mmol) oridonin, 0.51 ml 2,2-dimethoxypropane (4.12 mmol) and acetone mixture, stirred at room temperature for 6 Hour. Add sodium bicarbonate powder to neutralize and evaporate to dryness. The residue was purified with neutral alumina and eluted with PE:EA=1:1 to obtain 3.27 g of propylidene-protected orididenin (yield=98%) as a pure white solid powder. H1 NMR (CDCl3): 6.14(s, 1H), 5.73(d, J=11.2Hz, 1H), 5.54(s, 1H), 4.78(s, 1H), 4.23(d, J=10Hz, 1H), 4.05(d, J=10.0Hz, 1H), 3.91(m, 1H), 3.46(m, 1H), 3.05(d, J=8.8Hz, 1H), 2.53(m, 1H), 1.95(m, 1H ), 1.81-1.43 (m, 10H), 1.73 (s, 3H), 1.33 (s, 3H), 1.17 (s, 3H), 1.15 (s, 3H).

Embodiment 2

[0046] When R1 represents CO(CH 2 ) 2 CO 2When Na, R2, R3 and R4 represent H, the preparation of Oridonin A derivative shown in general formula 1: under nitrogen protection, 74mg succinic anhydride (0.74mmol) is added to 100mg propylidene protected Oridonin In a mixture of methyl element (0.247mmol) and pyridine, heated to 80°C, stirred for 24 hours, and evaporated to dryness. The residue was applied to a macroporous adsorption resin column AB-8, washed with water with a pH value of 4, then with water with a pH value of 7.0, and finally eluted with ethanol, and concentrated to obtain a white solid. The white solid was dissolved in methanol and strongly acidic cationic resin and stirred for 2 days, filtered, the filtrate was concentrated, purified by reverse phase column, eluted with methanol / water, and neutralized with NaOH to obtain Oridonin A Sodium Succinate. H1 NMR (D2O): 6.16(s, 1H), 5.68(s, 1H), 4.96(s, 1H), 4.33(d, J=10.4Hz, 1H), 3.70(d, J=6.0Hz, 1H) , 3.10(d, J=10....

Embodiment 3

[0048] When R1 represents PO 3 Na 2 , when R2, R3 and R4 represent H, the preparation of Oridonin A derivative shown in general formula 1: under nitrogen protection, 13 μl phosphorus oxychloride adds (0.15mmol) to 20mg propylidene protected Oridonin In a mixture of A (0.05 mmol) and pyridine, stirred at room temperature for 24 hours, and evaporated to dryness. The residue was applied to a macroporous adsorption resin column AB-8, washed first with water with a pH value of 4, then with water with a pH value of 7.0, and finally eluted with ethanol, and concentrated to obtain 15 mg of a white solid. The white solid was dissolved in methanol and strong acidic cationic resin and stirred for 2 days, filtered, the filtrate was concentrated, purified by reverse phase column, eluted with methanol / water, and neutralized with NaOH to obtain oridonin sodium phosphate. H1 NMR (D2O): 6.24(s, 1H), 5.77(s, 1H), 5.10(s, 1H), 4.36(d, J=10.4Hz, 1H), 4.20(d, J=10.4Hz, 1H) , 3.94(m, 1H), 3.79(d...

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Abstract

The invention discloses a water soluble oridonin derivative shown as a general formula (1) and preparation method thereof. Water soluble groups such as succinate, sulphosuccinic acid ester, sulphonic acid ester, and the like are added through the structure so as to greatly improve the water solubility and the medicinal property of the water soluble oridonin derivative.

Description

technical field [0001] The invention relates to oridonin, in particular to a water-soluble oridonin derivative and a preparation method thereof. Background technique [0002] Rubescens is derived from Rabdosia rubescens (Hemsl.) Hara, a plant of the genus Lamiaceae. In the 1970s, the Henan Provincial Institute of Medical Sciences, Henan Medical University and Yunnan Provincial Plant Research jointly conducted research on the chemical components, pharmacological effects and clinical efficacy of Rubescens japonicus. The main anti-cancer active ingredients - Oridonin and Ponicidin were found. The 1977 edition of "Pharmacopoeia of the People's Republic of China" included Donglingcao. Due to the good anti-tumor effect of the plant and its main active ingredients and their non-obvious toxicity in toxicity tests, Rubescens japonicus has attracted extensive attention from domestic and foreign medical scholars. [0003] Among the more than 100 diterpenoid components that have been...

Claims

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Application Information

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IPC IPC(8): C07D493/08C07F9/6561
CPCY02P20/55
Inventor 张健存
Owner SHENZHEN JYMED TECH
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