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Nodosin derivatives and preparation method and application thereof

A technology of derivatives and compounds, applied in the field of Nodosin derivatives and their preparation, can solve the problems of less research and achieve the effect of good anti-cancer activity

Active Publication Date: 2018-11-02
XINXIANG MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, little research has been done on derivatives of this compound

Method used

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  • Nodosin derivatives and preparation method and application thereof
  • Nodosin derivatives and preparation method and application thereof
  • Nodosin derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Synthesis of Nodosin Succinate (15)

[0016]

[0017] Add 106.7mg (0.29mmol) of Nodosin, 5mL dichloromethane, and 0.4mL (2.88mmol) triethylamine into a 100mL round-bottomed flask in sequence, and stir in a low-temperature reactor. Adjust the temperature to about 0°C. Diacid anhydride 117.2mg (1.17mmol), dissolved with a small amount of dichloromethane, the latter was slowly dropped into the former, after the drop was completed, placed at room temperature and stirred for 12h, adding a small amount of water to terminate the reaction, extracted twice with ethyl acetate 20mL, followed by Wash with dilute acid solution, wash with water, separate the organic layer, dry over anhydrous magnesium sulfate, and concentrate to obtain the crude product, which is separated by silica gel column chromatography (chloroform:methanol 20:1) to obtain the target compound with a yield of 49.3%.

[0018] HRMS-ESI(m / z): calcd for C 24 h 30 o 9 [M+Na] + 485.1793,found:485.1787; 1 H-NMR ...

Embodiment 2

[0020] Synthesis of Nodosin Glutarate Monoester (16)

[0021]

[0022] Add 118.0mg (0.33mmol) of Nodosin, 5mL dichloromethane, and 0.45mL (7.94mmol) triethylamine into a 100mL round-bottomed flask in sequence, and stir in a low-temperature reactor. Adjust the temperature to about 0°C. 148.8 mg (1.30 mmol) of dianhydride was dissolved in a small amount of dichloromethane, and the latter was slowly dripped into the former. After the dripping was completed, it was stirred at room temperature for 12 hours, and a small amount of water was added to terminate the reaction. Extracted twice with 20 mL of ethyl acetate, followed by Wash with dilute acid solution and water, separate the organic layer, dry over anhydrous magnesium sulfate, and concentrate to obtain the crude product, which is separated by silica gel column chromatography (chloroform:methanol 20:1) to obtain the target compound with a yield of 73.1%.

[0023] HRMS-ESI(m / z): calcd for C 25 h 32 o 9 [M+Na] + 499.1950,...

Embodiment 3

[0025] Synthesis of 6-Acetyl Nodosin(17)

[0026]

[0027]Add 138.4mg (0.38mmol) of Nodosin, 5mL dichloromethane, and 0.45mL (7.94mmol) triethylamine into a 100mL round-bottomed flask in turn, and stir in a low-temperature reactor. Adjust the temperature to about 0°C. Acid anhydride 0.4mL (4.23mmol), dissolved with a small amount of dichloromethane, the latter was slowly dropped into the former, after the drop was completed, placed at room temperature and stirred for 12h, adding a small amount of water to terminate the reaction, extracted twice with ethyl acetate 25mL, followed by Wash with dilute acid solution, wash with water, separate the organic layer, dry over anhydrous magnesium sulfate, and concentrate to obtain the crude product. The crude product is separated by silica gel column chromatography (dichloromethane:acetone 20:1) to obtain the target compound with a yield of 15.0%.

[0028] HRMS-ESI(m / z): calcd for C 22 h 28 o 7 [M+Na] + 427.1738,found:427.1729; 1 ...

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Abstract

The invention discloses Nodosin derivatives and a preparation method and the application thereof, and belongs to the technical field of medicinal chemistry. The invention discloses the Nodosin derivatives adopting a structural general formula as shown in the specification, and pharmaceutically acceptable salts thereof. The invention further specifically discloses the preparation method of the Nodosin derivatives and the application thereof to preparation of anticancer medicines. A Nodosin monomer compound with a rich source in the natural world is used as a precursor compound, molecular structure modification is performed under the premise of maintaining the original active center precursor under a simple mild synthesis condition, and different groups are introduced to synthesize a seriesof Nodosin derivatives; the synthesis process is simple and easy to control; a cytotoxic activity test indicates that the Nodosin derivatives have relatively good anticancer cell activity.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to a Nodosin derivative and a preparation method and application thereof. 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. Nodosin is a diterpenoid compound with a high content in Xihuangcao, and it is the active ingredient. Related studies have shown that Nodosin has a variety of biological activities, such as immune activity, anticancer activity, antibacterial effect, liver protection effe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10A61P35/00A61P35/02
CPCA61P35/00A61P35/02C07D493/10
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