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Enmein derivative and its preparation method and application

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

Active Publication Date: 2020-11-10
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 and its preparation method and application
  • Enmein derivative and its preparation method and application
  • Enmein derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Synthesis of Enmein Succinate (3)

[0017]

[0018] Add 117.2mg (0.32mmol) of Enmein, 5mL of acetonitrile, and 0.44mL (3.2mmol) of triethylamine into a 100mL round-bottomed flask in sequence, and stir in a low-temperature reactor. Adjust the temperature to about 0°C. Another succinic anhydride 128.2mg (1.28mmol), dissolved with a small amount of acetonitrile, the latter was slowly dropped into the former, after the drop was completed, placed at room temperature and stirred for 12h, added a small amount of water to terminate the reaction, extracted 3 times with 20mL of ethyl acetate, followed by dilute acid solution washing, washing with water, separating the organic layer, drying over anhydrous magnesium sulfate, and concentrating to obtain a crude product, which was 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:4...

Embodiment 2

[0021] Synthesis of Enmein Glutarate 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 in sequence, and stir in a low-temperature reactor. Adjust the temperature to about 0°C. 172.4mg (1.51mmol), dissolved with a small amount of acetonitrile, the latter was slowly dropped into the former, after the drop was completed, placed at room temperature and stirred for 12h, and a small amount of water was added to terminate the reaction, extracted 3 times with 20mL of ethyl acetate, followed by dilute acid solution washing, washing with water, separating the organic layer, drying over anhydrous magnesium sulfate, and concentrating to obtain a crude product, which was separated 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;...

Embodiment 3

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

[0027]

[0028] Add 121.0mg (0.33mmol) of Enmein, 5mL tetrahydrofuran, and 0.45mL (3.25mmol) of triethylamine into a 100mL round-bottomed flask in sequence, and stir in a low-temperature reactor. Adjust the temperature to about 0°C. mL (1.90mmol), dissolved with a small amount of tetrahydrofuran, the latter was slowly dropped into the former, after the drop was completed, it was left to stir at room temperature for 12h, and a small amount of water was added to terminate the reaction, extracted twice with 25mL of ethyl acetate, washed with dilute acid solution successively , washed with water, the organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product, which 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; 1H-...

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Abstract

The invention discloses an Enmein derivative, its preparation method and application, and belongs to the technical field of medicinal chemistry. An Enmein derivative with the general structural formula as follows and a pharmaceutically acceptable salt thereof: the invention also specifically discloses the preparation method of the Enmein derivative and its application in the preparation of anticancer drugs. The present invention uses the Enmein monomer compound with abundant natural sources as the precursor compound, adopts simple and mild synthesis conditions, carries out molecular structure modification while maintaining the original active center precursor, introduces different groups, synthesizes a series of Enmein derivatives, and synthesizes The process is simple and easy to control, and the test of cytotoxic activity shows that the Enmein derivative has better anticancer activity.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to an Enmein derivative and its preparation method and application. Background technique [0002] Rabdosia Serra (Maxim.) Hara is a plant of the genus Isodon in the family Labiatae. In folklore, Rabdosia Serra (Maxim.) Hara is widely used as a herbal medicine. It has the effects of clearing heat and dampness, reducing jaundice and dampness, cooling blood and dissipating blood stasis, etc. It is mainly used for the treatment of acute jaundice hepatitis, acute cholecystitis, damp-heat dysentery, enteritis, bruises and bruises, and health care, etc. It has good medicinal properties value. Enmein is a diterpenoid compound with a high content in Xihuangcao, and it is the active ingredient. Relevant studies have shown that Enmein has a variety of biological activities, such as immune activity, anticancer activity, antibacterial effect and so on. However, Enmein ...

Claims

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Application Information

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Patent Type & Authority Patents(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