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Triptolide alcohol derivative and its use

A technology for triptolide and derivatives is applied in the field of structural modification and activity research of active ingredients of natural medicines, and can solve problems such as limited application, toxic and side effects of triptolide, etc.

Inactive Publication Date: 2004-07-14
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the toxic and side effects of triptolide limit its clinical application.

Method used

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  • Triptolide alcohol derivative and its use
  • Triptolide alcohol derivative and its use
  • Triptolide alcohol derivative and its use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment 1 (5R)-5-hydroxy triptolide ketone

[0065]

[0066] Dissolve triptolide (374mg, 1.04mmol) in 20ml DMSO, then add SeO 2 (461mg, 4.16mmol), heated under slight reflux for 10 hours. The reaction system was cooled to room temperature, filtered, the filter residue was washed with ethyl acetate, the washing liquid was combined with the filtrate, and the solvent was evaporated under reduced pressure. The residue was saturated with Na 2 CO 3 Dissolved, extracted with ethyl acetate, the organic phase was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a white solid (5R)-5-hydroxytriptolide ketone (319mg, 0.85mmol, yield 82%).

[0067] 1 H-NMR (DMSO-d 6 , 400MHz) δ4.88(m, 2H), 4.11(d, J=2.9Hz, 1H), 4.08(d, J=2.9Hz, 1H), 3.42(d, J=4.4Hz, 1H), 2.24( Septet, J=6.9zHz, 1H), 1.96-2.20(m, 4H), 1.83(ddd, J=6.4, 11.7, 11.8Hz, 1H), 1.08(broad, dd, J=5.2, 12.4Hz, 1H ), 0.91(s,...

Embodiment 2

[0068] Example 2 (5R)-5-hydroxy triptolide and (5R)-5-hydroxy epitriptolide

[0069]

[0070] To a suspension of (5R)-5-hydroxytriptolide (20 mg, 0.053 mmol) dissolved in 5 mL of methanol was added NaBH 4 (8mg, 0.21mmol), stirred for 2 hours, the reaction system became a colorless clear solution, the solvent was evaporated under reduced pressure, the residue was dissolved in ethyl acetate, washed with water and saturated brine respectively, dried over anhydrous sodium sulfate, and reduced pressure The solvent was evaporated to dryness, and the residue was separated by column chromatography (eluent: cyclohexane: ethyl acetate = 1:1) to obtain (5R)-5-hydroxytriptolide (7.5mg, 0.02mmol, yield 38 %) and (5R)-5-hydroxyepitriptolide (11.3 mg, 0.03 mmol, yield 56%).

[0071] (5R)-5-Hydroxytriptolide:

[0072] 1 H-NMR (DMSO-d 6 , 400Hz) δ5.32(s, 1H), 4.87(m, 2H), 4.57(br.s, 1H), 3.73(d, J=2.9Hz, 1H), 3.53(d, J=2.9Hz, 1H ), 3.38(s, 1H), 3.34(d, J=5.0Hz, 1H), 2.07-2.19(m, 4H), 1...

Embodiment 3

[0075] Example 3 Δ 5，6 - Dehydrotriptolide

[0076]

[0077] Add (5R)-5-hydroxytriptolide ketone (224mg, 0.60mmol) into a solution of anhydrous pyridine (4ml, 50.57mmol) in dichloromethane (10ml), stir to dissolve, and then add trifluoro Acetic anhydride (600 mg, 2.85 mmol) was reacted at room temperature for 12 hours, and after thin layer chromatography (cyclohexane: ethyl acetate = 1: 1) checked that the raw materials disappeared, the reaction was terminated, the solvent was distilled off under reduced pressure, and the residue was distilled off with water (20 ml ) was diluted, added ethyl acetate (40ml × 3) for extraction, the organic phase was washed with dilute sulfuric acid, saturated sodium bicarbonate solution and saturated brine respectively, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain a brownish-yellow oil. Analysis and separation (eluent: cyclohexane: ethyl acetate = 3: 1), recrystallization from cyclohexane-ethyl acetate to giv...

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Abstract

The present invention is triptolide alcohol derivative, its pharmaceutically acceptable salt and optical isomer, their synthesis process and the application as antiphlogistic, immunological regulator and relevant disease treating agent.

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 synthesis of triptolide diterpenoid lactone-triptolide derivatives and the research on pharmacological activities such as anti-inflammation and immunosuppression. Background technique [0002] Tripterygium Wilfordii Hook f is a woody vine of the genus Tripterygium in the family Euonymus. It grows in the dark and humid places on the edge of mountain forests, and is distributed in the south of the Yangtze River Basin and the southwest region. Its chemical components are mainly diterpenes, triterpenes, and sesquiteres. terpenes, alkaloids, etc. Studies in the past two decades have shown that Tripterygium wilfordii has anti-inflammatory, immunosuppressive, anti-fertility, anti-tumor, antibacterial and other activities, especially in terms of immunosuppression, the diterpenoid lactone triptolide represented by the f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/34A61P9/10A61P17/00A61P37/02A61P37/06A61P37/08C07D493/22
CPCC07D493/22A61K31/34A61P17/00A61P37/02A61P37/06A61P37/08A61P9/10
Inventor 李援朝左建平张凡周茹丁建
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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