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Preparation method of germacrone oxobutyric acid

A technology of gemmanone oxobutyric acid and gemmanone, which is applied in the field of preparation of gemmanone oxobutyric acid, can solve problems such as no preparation method reported in literature, difficulty in structural modification, and not being particularly stable, and achieves low cost , easy structural modification and transformation, mild reaction conditions

Inactive Publication Date: 2018-11-06
SOUTHEAST UNIV CHENGXIAN COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the structure of gemmacone contains double bonds, it is not particularly stable, the reaction is easy to open the ring, and the structure modification is difficult
However, there is no literature reporting this type of compound and its preparation method at present

Method used

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  • Preparation method of germacrone oxobutyric acid
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  • Preparation method of germacrone oxobutyric acid

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Experimental program
Comparison scheme
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Embodiment 1

[0015] Embodiment 1: the synthesis of gemmacone reduction product (compound I)

[0016]

[0017] Nitrogen protection, the LiAlH 4 (70mg, 1.835mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -15°C, under vigorous stirring, slowly added dropwise a tetrahydrofuran solution of gemmaconone (100mg, 0.459mmol), stirred for 10min, and reacted in an ice bath for 2h (monitored by TLC). Add 15% sodium hydroxide solution and anhydrous sodium sulfate, stir for 5 minutes, filter, wash the filter cake with dichloromethane, and spin the filtrate to obtain a crude product, which is separated and purified by column chromatography (PE:EA=10:1) to obtain Compound I, a colorless oil. NMR data ( 1 HNMR, 400MHz, internal standard TMS, solvent DMSO-d6) as follows: δppm 4.67 (s, 1H, OH), 4.58 (m, 1H, CH), 3.10 (q, J=10.4Hz, 1H, CH), 2.22 ( m,3H,CH),2.08-1.67(m,6H,CH 2 ),1.60(s,6H,CH 3 ),1.45(s,6H,CH 3 ).

Embodiment 2

[0018] Embodiment 2: the synthesis of gemmaconone oxobutanoic acid (compound II)

[0019]

[0020] Nitrogen protection, in a 100mL single-necked flask, add gemmaconone reduction product (compound I, 120mg, 0.545mmol), succinic anhydride (54.6mg, 0.545mmol), DMAP (80mg, 0.655mmol) and 10mL of anhydrous tetrahydrofuran, 75 °C and stirred overnight. After filtration, the filtrate was spin-dried, separated and purified by column chromatography (PE: EA = 1: 1) to obtain compound II as a colorless oil. NMR data ( 1 HNMR, 400MHz, internal standard TMS, solvent DMSO-d6) as follows: CH),2.72-2.63(m,4H,CH 2 ), 2.28 (d, J=11.6Hz, 2H, CH 2 ),2.16-2.08(m,6H,CH 2 ),1.84(s,3H,CH 3 ),1.76(s,3H,CH 3 ),1.74(s,3H,CH 3 ),1.68(s,3H,CH 3 ).

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Abstract

The invention relates to a preparation method of germacrone oxobutyric acid. The preparation method is characterized by comprising the following step: reacting a germacrone reducing product I with substituted succinic anhydride to prepare the germacrone oxobutyric acid II. A compound II is synthesized by adopting the preparation method for the first time, the reaction condition is mild, the operation is simple, the raw material is easy to obtain, the cost is relatively low, the subsequent structure modification and transformation are facilitated since the germacrone oxobutyric acid contains along-chain carboxyl, and the preparation method has important theoretical and practical significance in developing a novel curcuma zedoaria antitumor drug.

Description

technical field [0001] The invention belongs to the field of drug design and synthesis. In particular, it relates to a preparation method of gemaconone oxobutanoic acid. technical background [0002] Gemacone is a sesquiterpene compound extracted from Zedoary Curcuma, which has pharmacological activities such as anti-inflammatory, antibacterial, antithrombotic, liver-protecting and choleretic, and anti-cancer. At present, there are few reports on its structural characteristics, structure-activity relationship, and derivatization at home and abroad, and most of them are content determination and pharmacological studies. Since the structure of gemmacone contains double bonds, it is not particularly stable, and the reaction is easy to open the ring, and the structure modification is difficult. However, there is currently no literature reporting such compounds and their preparation methods. [0003] In view of the potential medicinal value of gemmacone, the present invention ...

Claims

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Application Information

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IPC IPC(8): C07C69/40C07C67/08
CPCC07C29/159C07C67/08C07C2601/18C07C35/205C07C69/40
Inventor 刘媛媛吕坤志南秋利余璐张亚安
Owner SOUTHEAST UNIV CHENGXIAN COLLEGE
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