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Triptolide derivatives substituted with double bonds and their preparation methods and applications

A technology of triptolide and derivatives, which is applied in the field of structural modification and activity research of active ingredients of natural medicines, and can solve the problems of increased difficulty in synthesis and separation

Active Publication Date: 2017-07-04
SHANGHAI HUILUN BIOLOGICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Simultaneously in p-triptolide C 14 When the - position was modified, it was found that the group configuration at this position had a significant impact on the activity of the compound, and the problem of optical isomers added great difficulty to the synthesis and separation.

Method used

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  • Triptolide derivatives substituted with double bonds and their preparation methods and applications
  • Triptolide derivatives substituted with double bonds and their preparation methods and applications
  • Triptolide derivatives substituted with double bonds and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of Structural Formula (Ia) 14-Dehydroxyl-14-Methylene-5-Hydroxy Triptolide

[0038] step 1

[0039] Preparation of structural formula (2) (14S)-14β-methyl epitriptolide

[0040]

[0041] Under the protection of argon, add 10mL of anhydrous ether into the reaction flask containing magnesium chips (264mg, 11mmol), and add MeI (1.42g, 10mmol) dissolved in 5mL of anhydrous ether dropwise to the above reaction system through a constant pressure dropping funnel middle. After the addition, the dark gray reaction system was stirred at room temperature for half an hour. Take 1.37 mL of freshly prepared MeMgI format reagent solution and add dropwise to triptolide ketone 1 (90 mg, 0.25 mmmol) that has been dissolved in 8 mL of dry THF. After reacting at room temperature for 2 hours, the reaction was stopped, the reaction system was quenched with saturated ammonium chloride solution, extracted with ethyl acetate, the organic phase was washed with saturated brine, ...

Embodiment 2

[0051] Preparation of 14-dehydroxyl-14-methylene-15-hydroxytriptolide of structural formula (Ib)

[0052] step 1

[0053] Preparation of 14-dehydroxyl-14-methylene-15-hydroxytriptolide of structural formula (Ib)

[0054]

[0055] The stock solution (50 mM) of 14-dehydroxy-14-methylene triptolide 3 was prepared in methanol, and the methanol content in the final incubation system was 0.1%. The volume of a single incubation system is 10 mL, and the medium is 100 mM phosphate buffer (PBS, pH 7.4), including rat liver microsomal protein at a final concentration of 0.5 mg / mL, 50 μM 14-dehydroxyl-14-methylene raptor Cane lactone 3 and 1mM NADPH were incubated in a water bath at 37°C for 2h. Extract 14-dehydroxyl-14-methylene triptolide 3 rat liver microsome hatching solution with ethyl acetate, concentrate under reduced pressure at 40°C to remove solvent, dissolve in 5ml methanol:water 65:35, and pass through Semi-preparative HPLC separation, collected fractions, and concentrat...

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PUM

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Abstract

Disclosed are a double-bond substituted tripterygium wilfordii lactone derivative as represented by formula (I), or pharmaceutically acceptable salt or hydrate thereof, or optical isomer thereof, wherein R1=OH, R2=H, or R1=H, R2=OH. Also disclosed are a preparation method and uses thereof in the preparation of drugs for treating cancers and cancer-related diseases.

Description

technical field [0001] The invention relates to the structural modification and activity research of the active ingredients of natural medicines, in particular to the double-bond substituted triptolide derivatives, their preparation methods and the research on the treatment of proliferative tumor diseases. Background technique [0002] Tripterygium wilfordii, commonly known as Broken Heart Grass, is a woody vine of the genus Tripterygium genus Celastraceae, and is a plant with relatively abundant resources in my country. There are four kinds of Tripterygium plants, namely Tripterygium wilfordii Hook f., Tripterygium hypoglaucumLevl. Hutch, Tripterygium regelii Sprague et Takeda and Tripterygium regelii Sprague et Takeda (Tripterygium forretii Dicls), are distributed in our country. Tripterygium wilfordii was first recorded in "Shen Nong's Materia Medica", and its main chemical components include diterpenes, triterpenes, sesquiterpenes, alkaloids, etc. So far, nearly 200 com...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J73/00A61K31/585A61P35/00
CPCA61P35/00C07J73/003
Inventor 樊兴秦继红
Owner SHANGHAI HUILUN BIOLOGICAL TECH CO LTD
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