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Beta-elemene halide and preparation method therefor

A technology of elemene and halogenated products, which is applied in the field of β-elemene halogenated products and its preparation, can solve the problems of complex synthesis methods, inability to separate mixtures, and difficulties in separation and purification of mixtures, and achieve high yield and easy operation Effect

Active Publication Date: 2020-01-14
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In summary, the synthesis methods of β-elemene halides reported in the existing literature are complicated, and many compounds obtained exist in the form of mixtures, which are difficult to separate and purify, and some mixtures cannot even be separated at all.

Method used

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  • Beta-elemene halide and preparation method therefor
  • Beta-elemene halide and preparation method therefor
  • Beta-elemene halide and preparation method therefor

Examples

Experimental program
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Effect test

Embodiment 1

[0068] Embodiment 1: the preparation of the mixture of 13-chloro β-elemene (2) and 14-chloro β-elemene (3) (sodium hypochlorite and cerium chloride system)

[0069]

[0070] To a solution of β-elemene starting material (218mg, 1.069mmol) in dichloromethane (5mL) and water (5mL) in an ice bath, tetrabutylammonium iodide (197mg, 0.53mmol) and tributylammonium heptahydrate were added. Cerium chloride (1.153 g, 3.09 mmol). Then sodium hypochlorite (1.2 mL, content 8-13%, 3.207 mmol) was slowly added dropwise to the above mixture. The reaction solution was kept cooled in an ice bath, stirred for 0.5 hours, and reacted overnight at room temperature. The starting material was completely reacted by thin-plate chromatography, and the mixture was extracted with ethyl acetate (3 x 5 mL). The combined organic phases were washed successively with water (2 x 5 mL) and saturated brine (2 x 5 mL), and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, the filt...

Embodiment 2

[0072] Embodiment 2: the preparation of the mixture of 13-chloro β-elemene (2) and 14-chloro β-elemene (3) (sodium hypochlorite and cerium chloride system)

[0073]

[0074] To a solution of β-elemene starting material (218mg, 1.069mmol) in dichloromethane (5mL) and water (5mL) in an ice bath, tetrabutylammonium iodide (197mg, 0.53mmol) and tributylammonium heptahydrate were added. Cerium chloride (1.153 g, 3.09 mmol). Then sodium hypochlorite (1.2 mL, content 8-13%, 3.207 mmol) was slowly added dropwise to the above mixture. The reaction solution was kept cooled in an ice bath, stirred for 0.5 hours, and reacted overnight at room temperature. The starting material was completely reacted by thin-plate chromatography, and the mixture was extracted with ethyl acetate (3 x 5 mL). The combined organic phases were washed successively with water (2 x 5 mL) and saturated brine (2 x 5 mL), and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, the filt...

Embodiment 3

[0075] Example 3: Preparation of a mixture of 13-chloro-β-elemene (2) and 14-chloro-β-elemene (3) (NCS and cerium chloride system)

[0076]

[0077] To a solution of β-elemene starting material (201.1 mg, 1.03 mmol) in acetic acid (3 mL) was added NCS (136.7 mg, 1.00 mmol) under ice bath (10-15°C). The reaction solution was kept ice-bath cooled (10-15°C), stirred for 8 hours, thin plate chromatography detected that the raw materials were not completely reacted, and reacted overnight at room temperature (25-28°C. The reaction was slowly added dropwise with saturated sodium bisulfite (7.5mL) and Quenched with water (8mL), the mixture was extracted with petroleum ether (3 x 5mL). The combined organic phase was washed successively with saturated sodium bisulfite (3 x 5mL), water (3 x 5mL) and saturated brine (3 x 5mL) , and dried with anhydrous sodium sulfate. The desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the resulting crude ...

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Abstract

The invention provides a beta-elemene halide, a preparation method therefor and an application of the beta-elemene halide. Specifically, the invention provides a preparation method for a compound witha structure represented by a formula I shown in the description, wherein each group is as defined in the description. The invention further provides a compound with a structure represented by a formula II shown in the description (each group is as defined in the description), a pharmaceutical composition containing the compound represented by the formula II, the compounds and isotope derivatives,chiral isomers, allosteric isomers, different salts, prodrug, preparations and the like of these compounds. The compounds can serve as intermediates and be used for preparing derivatives of elemene and treating various diseases capable of being treated by the elemene, including lung cancer, mammary cancer, liver cancer, and the like.

Description

technical field [0001] The invention belongs to the field of preparation of intermediates of β-elemene derivatives, and in particular relates to a β-elemene halogenated product and a preparation method thereof. Background technique [0002] Elemis is a sesquiterpene compound extracted and isolated from Curcuma curcuma. Compared with paclitaxel, hydroxycamptothecin, vinblastine and other plant anticancer drugs, it has the advantages of the smallest molecular weight, the smallest toxicity, and a broad spectrum of anti-tumor effects. 1994 In 2009, the State Food and Drug Administration approved it as an anti-tumor plant drug with independent intellectual property rights in my country. The emulsion with elemene as the main component has been approved by the Ministry of Health in 2008 as a national second-class anti-cancer new drug and has entered the second-phase clinical research. This new anti-tumor natural product has gradually shown strong clinical efficacy in various tumors....

Claims

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Application Information

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IPC IPC(8): C07C17/02C07C22/04
CPCC07C17/10C07C17/389C07C22/00A61P35/00C07C2601/14C07B2200/07Y02P20/55
Inventor 谢恬叶向阳李震高园卓晓韬戚香
Owner HANGZHOU NORMAL UNIVERSITY
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