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Method for preparing parthenolide by using costunolide as raw material

A kind of technology of parthenolide and woody lactone, which is applied in the field of medicine

Active Publication Date: 2015-03-18
ACCENDATECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Cosmolides also belong to sesquiterpene lactones, and there is no literature report on the preparation of parthenolide from coosmanthus lactones.

Method used

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  • Method for preparing parthenolide by using costunolide as raw material
  • Method for preparing parthenolide by using costunolide as raw material
  • Method for preparing parthenolide by using costunolide as raw material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Preparation of compound 1:

[0015] Under the protection of nitrogen, dissolving coynelide (1.39g, 6mmol) in dried toluene, cooled to zero, slowly added 1M diisobutylaluminum hydride dichloromethane solution (24mL, 24mmol), after the addition was complete Stirring was continued for four hours at room temperature. After TLC detected that the reaction was substantially complete, it was quenched with 10% sodium potassium tartrate solution (10 mL), filtered a layer of diatomaceous earth, and the aqueous phase was extracted three times with ether, and the combined organic layers were washed with saturated brine. Dry over anhydrous sodium sulfate. After filtration and purification by column chromatography, compound 1 (1.11 g, 79%) was obtained.

[0016]

[0017] Molecular formula: C 15 h 24 o 2

[0018] Molecular weight: 236

[0019] Appearance: colorless oily

[0020] Spectral data:

[0021] δ 1 HNMR (400MHz, CDCl 3 )δ5.16(s, 1H), 5.01(s, 1H), 4.79(brd, J=10.4Hz...

Embodiment 2

[0023] Preparation of Compound 2:

[0024] Under nitrogen protection, compound 1 (115mg, 0.487mmol), 4-dimethylaminopyridine (6mg, 0.0487mmol), triethylamine (0.12mL, 0.818mmol) were dissolved in dry dichloromethane (2.3mL), Cool to zero, add 0.54M trimethylchlorosilane dichloromethane solution (1mL, 0.54mmol), stir for 4 hours, add saturated brine (2.4mL) to terminate the reaction, and extract the aqueous layer with dichloromethane (5mL) three times, It was dried over sodium sulfate, filtered, concentrated and purified by column chromatography to obtain compound 2 (159 mg, 93%).

[0025]

[0026] Molecular formula: C 21 h 38 o 2 Si

[0027] Molecular weight: 350

[0028] Appearance: colorless oily

[0029] Spectral data:

[0030] 1 HNMR (400MHz, CDCl 3 )δ5.16(s, 1H), 5.00(s, 1H), 4.80(brd, J=10.0Hz, 1H), 4.64(brd, J=9.6Hz, 1H), 4.21-4.06(m, 3H), 2.66(s, 1H), 2.40-2.30(m1H), 2.29-2.16(m, 2H), 2.16-2.01(m, 3H), 2.01-1.92(m, 1H), 1.71-1.62(m, 5H), 1.41(s, 3H), 0.93...

Embodiment 3

[0032] Preparation of Compound 3:

[0033] method 1:

[0034] Under nitrogen protection, add 723mg activated Molecular sieves and 19 mL of dried dichloromethane. Cool to -4 degrees, add diisopropyl tartrate (60μL, 0.28mmol), stir for ten minutes, add titanium tetraisopropoxide (70μL, 0.24mmol), stir for 15 minutes, then add 3.3mol / L peroxide tert-butanol toluene solution (1.1mL, 3.63mmol), after stirring for 30 minutes, compound 2 ((817mg, 2.35mmol) was dissolved in 4mL of dried dichloromethane and added, the reaction temperature was raised to -18 degrees, Stir for 12 hours, add acetone (20mL) containing 2% water to quench the reaction, rise to room temperature and stir for 3 hours, filter a layer of diatomaceous earth, dry the filtrate with anhydrous magnesium sulfate, filter and concentrate to pass through the column to obtain compound 3 (607mg , 71%)

[0035] Method 2:

[0036] Dissolve compound 2 (220mg, 0.63mmol) in dichloromethane (15mL), add vanadyl acetylacetonat...

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Abstract

The invention relates to a method for preparing parthenolide, and in particular relates to a method for synthesizing parthenolide by using costunolide as a raw material through the following reaction steps in the specification.

Description

technical field [0001] The invention belongs to the technical field of medicines, specifically, a method for preparing parthenolide by using woody lactone as a raw material. Background technique [0002] Parthenolide, a sesquiterpene lactone compound, is a compound extracted from feverfew, which was originally used to treat skin infections, rheumatism and migraine. Recent studies have shown that parthenolide can inhibit the growth of cancer cells such as prostate cancer, breast cancer, gastric cancer, leukemia cancer, kidney cancer, lung cancer, colon adenocarcinoma, and medulloblastoma. Can treat skin cancer caused by ultraviolet rays. The study of its mechanism of action found that parthenolide can inhibit the activation of transcription factor NF-κB, and its activity may mainly come from the Michael addition reaction between the sulfhydryl group on Cys38 of the p65 / NF-κB subunit and parthenolide Since NF-κB is an important gene regulating tumor invasion, metastasis, and...

Claims

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Application Information

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IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 陈悦张泉龙菁
Owner ACCENDATECH
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