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Semisynthesis method of 17-hydroxyjolkinolide B

A semi-synthetic technology of euphorbia lactone, applied in the direction of organic chemistry and the like, can solve the problem that the yield is only 7-16%, and achieve the effects of reducing the treatment cost, increasing the market supply and reducing the production cost.

Active Publication Date: 2015-06-03
QIQIHAR UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, Paul A.Wender of Stanford University in the United States successfully synthesized crotane diterpene prostratin and its analogs through phorbol from croton oil through multi-step reactions, but the yield was only 7-16%.

Method used

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  • Semisynthesis method of 17-hydroxyjolkinolide B
  • Semisynthesis method of 17-hydroxyjolkinolide B
  • Semisynthesis method of 17-hydroxyjolkinolide B

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Embodiment 1

[0037] Embodiment one, figure 1 It is the semi-synthetic route 1 diagram of 17-hydroxy-petrolactone B (17-hydroxyjolkinolide B) of the present invention, and the reaction steps are as follows figure 1 Shown:

[0038] Preparation of Jolkinolide B (Compound 2)

[0039] image 3 It is the semi-synthetic route figure of rock euphorbia lactone B (Jolkinolide B) of the present invention, as image 3 As shown, dissolving Jolkinolide A (204.0mg, 0.6mmol) in dichloromethane (200.0mL) to form a 0.03mol / L solution, adding m-CPBA (206.0mg, 2.0eq ), stirring at room temperature, after reacting for 4h, adding 10% Na 2 S 2 o 3 Aqueous solution (100 mL) quenched the reaction. It was extracted with ethyl acetate (3×100 mL), and the ethyl acetate layer was washed with saturated brine (200 mL), dried over anhydrous sodium sulfate, filtered and concentrated to obtain 312.0 mg of a crude product. The product was separated by silica gel column chromatography and eluted with Hexane / EtOAc=8 / 2 (...

Embodiment 2

[0046] Embodiment two, figure 2 It is the semi-synthetic route 2 figure of 17-hydroxyl-petrolactone B (17-hydroxyjolkinolide B) of the present invention, and the reaction steps are as follows figure 2 Shown:

[0047] Compound 3 (22.1 mg, 0.06 mmol) was dissolved in DMSO (2.5 mL), and water (0.3 mL) was added, and stirred at room temperature. After reacting for 72h, add saturated NaHCO 3 Aqueous solution (10 mL) quenched the reaction. with CHCl 3 (10 mL×4) extraction. The organic phases were combined, washed with saturated brine (30.0 mL×4), and dried over anhydrous sodium sulfate. Filtration and concentration under reduced pressure gave 20.3 mg of crude product. The product was separated and purified by column chromatography, Hexane / EtOAc=6 / 4 (100mL) was eluted, and the target product 17-hydroxyjolkinolide B (17-hydroxyjolkinolide B) (16.5mg) was obtained, and the yield was 74 %.

[0048] Figure 4 It is the compound Jolkinolide A (Jolkinolide A) 1 H NMR diagram, ...

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Abstract

The invention provides a semisynthesis method of 17-hydroxyjolkinolide B. The semisynthesis method comprises the following steps: carrying out a cyclization reaction on a double bond at the C11 position of an epoxy ring of Jolkinolide A serving as a raw material; bromizing a methyl at the C17 position of a lactonic ring, then carrying out debromination and acetylation, and finally hydrolyzing an acetyl to obtain 17-hydroxyjolkinolide B. The invention discloses a new method for synthesizing 17-hydroxyjolkinolide B and provides a basis for research and development of jolkinolide type medicines. The successful synthesis of 17-hydroxyjolkinolide B provides a new direction for research of anti-cancer drugs. The method has the advantages that the yield of 17-hydroxyjolkinolide B can be improved, the production cost can be reduced, the market supply is enlarged and the cancer treatment cost is lowered.

Description

technical field [0001] The invention relates to the field of medicine synthesis, in particular to a semi-synthetic method of euphorlide 17-hydroxy-petrolide B (17-hydroxyjolkinolide B). Background technique [0002] Cancer, also known as malignant tumors in medical terms, is a large class of diseases caused by abnormal control of cell growth and proliferation mechanisms, and has become one of the diseases that seriously endanger human health. Among them, leukemia is a kind of malignant clonal disease of hematopoietic stem cells. Clonal leukemia cells proliferate and accumulate in bone marrow and other hematopoietic tissues due to mechanisms such as uncontrolled proliferation, differentiation disorder, and apoptosis inhibition, and infiltrate other tissues and organs, while normal hematopoiesis is inhibited. In China, the incidence rate of leukemia in each region occupies the sixth place among all kinds of tumors. Effects of two diterpene monomer compounds, Jolkinolide B an...

Claims

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Application Information

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IPC IPC(8): C07D493/20
CPCC07D493/20
Inventor 李军赵明张晓红撖志明贾丽娜王金兰王建飞张树军
Owner QIQIHAR UNIVERSITY
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