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Nodosin derivative and its preparation method and application

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

Active Publication Date: 2021-04-16
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 derivative and its preparation method and application
  • Nodosin derivative and its preparation method and application
  • Nodosin derivative and its preparation method and application

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

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 Patents(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