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Enmein derivative as well as preparation method and application thereof

A technology of derivatives and compounds, applied in the field of medicinal chemistry, can solve the problems of easy destruction, disappearance, less research, etc., and achieve the effect of good anti-cancer activity.

Active Publication Date: 2018-11-23
XINXIANG MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These two structures are not very stable, and the violent reaction environment is easy to destroy their structures, which may weaken or disappear their activity. Therefore, there are few studies on the derivatives of this compound

Method used

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  • Enmein derivative as well as preparation method and application thereof
  • Enmein derivative as well as preparation method and application thereof
  • Enmein derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Synthesis of Enmein Succinic Acid Monoester (3)

[0017]

[0018] Enmein 117.2mg (0.32mmol), acetonitrile 5mL, triethylamine 0.44mL (3.2mmol) were added to a 100mL round-bottomed flask in turn, placed in a low-temperature reactor and stirred, adjust the temperature to about 0℃, and take succinic anhydride 128.2mg (1.28mmol), dissolved in a small amount of acetonitrile, slowly drip the latter into the former, after dripping, leave it at room temperature and stir for 12h, add a small amount of water to terminate the reaction, extract 3 times with 20mL ethyl acetate, and then use dilute acid solution Wash, wash with water, separate the organic layer, dry with anhydrous magnesium sulfate, and concentrate to obtain a crude product. The crude product is separated by silica gel column chromatography (chloroform:methanol 20:1) to obtain the target compound with a yield of 43.6%.

[0019] HRMS-ESI(m / z):calcd for C 24 H 30 O 9 [M+Na] + 485.1793,found:485.1783; 1 H-NMR(400MHz, C 5 D 5 ...

Embodiment 2

[0021] Synthesis of Enmein Glutaric Acid Monoester (4)

[0022]

[0023] Add 138.2mg (0.38mmol) of Enmein, 5mL of acetonitrile, and 0.52mL (3.75mmol) of triethylamine into a 100mL round-bottomed flask, place in a low temperature reactor and stir, adjust the temperature to about 0℃, and take glutaric anhydride 172.4mg (1.51mmol), dissolved in a small amount of acetonitrile, slowly drip the latter into the former, after dripping, leave it at room temperature and stir for 12h, add a small amount of water to stop the reaction, extract 3 times with 20mL ethyl acetate, and then use dilute acid solution Washing, washing with water, separating the organic layer, drying with anhydrous magnesium sulfate, and concentrating to obtain the crude product, and separating the crude product by silica gel column chromatography (chloroform:methanol 20:1) to obtain the target compound with a yield of 62.7%.

[0024] HRMS-ESI(m / z):calcd for C 25 H 32 O 9 [M+Na] + 499.1950,found:499.1944; 1 H-NMR(400MHz,...

Embodiment 3

[0026] Synthesis of 6-acetyl Enmein(5)

[0027]

[0028] Enmein 121.0mg (0.33mmol), tetrahydrofuran 5mL, triethylamine 0.45mL (3.25mmol) were added to a 100mL round-bottom flask in turn, placed in a low temperature reactor and stirred, adjust the temperature to about 0℃, and take acetic anhydride 0.18 mL (1.90mmol), dissolve with a small amount of tetrahydrofuran, slowly drip the latter into the former, after dripping, leave it at room temperature and stir for 12h, add a small amount of water to terminate the reaction, extract twice with ethyl acetate 25mL, and wash with dilute acid solution in turn , Washed with water, separated the organic layer, dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was separated by silica gel column chromatography (dichloromethane:acetone 16:1) to obtain the target compound with a yield of 32.9%.

[0029] HRMS-ESI(m / z):calcd for C 22 H 28 O 7 [M+Na] + 427.1738,found:427.1741; 1 H-NMR (400MHz, CDCl ...

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Abstract

The invention discloses an Enmein derivative as well as a preparation method and application thereof, and belongs to the technical field of pharmaceutical chemistry. The Enmein derivative shown in thefollowing structural general formula and pharmaceutically-acceptable salt are as follows: the formula (1) is shown in the description. The invention also specially discloses the preparation method ofthe Enmein derivative and the application of the Enmein derivative in preparation of anti-tumor medicines. By using an Enmein monomer compound which is rich in sources in the natural world as a precursor compound, a simple and mild synthetic condition is adopted, molecular structure modification is carried out under the premise of maintaining an original activity center precursor, different groups are introduced, and series Enmein derivatives are synthesized; moreover, the synthetic process is simple and is easily controlled; a cell toxic activity test proves that the Enmein derivative has higher anti-tumor cell activity.

Description

Technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to an Enmein derivative and a preparation method and application thereof. Background technique [0002] Rabdosia Serra (Maxim.) Hara is a plant of the Labiatae genus Isodon. In folk, Rabdosia Serra (Maxim.) Hara is widely used as a herbal medicine. Its whole plant is used as medicine, and it tastes bitter and cool. It has the functions of clearing heat and dampness, relieving yellowness and dampness, cooling blood and dispersing blood stasis, etc. It is mainly used for the treatment of acute jaundice hepatitis, acute cholecystitis, damp-heat dysentery, enteritis, bruises and swelling and health care, etc. It has good medicinal use value. Enmein is a diterpenoid compound with a high content in Xihuangcao, which is the active ingredient. Related studies have shown that Enmein has a variety of biological activities, such as immune activity, anti-cancer activity, ant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10C07F9/6561A61P35/00A61P35/02
CPCA61P35/00A61P35/02C07D493/10C07F9/6561
Inventor 尚校军张崇蒋燕赵杰邵芃卢慧娟闫福林闫建伟刘静高云慧
Owner XINXIANG MEDICAL UNIV