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Neogambogic acid derivative, preparation method thereof and pharmaceutical application

A technology of new gambogic acid and derivatives, applied in the fields of medicinal chemistry and drug therapy, can solve the problems of low solubility of new gambogic acid and influence on medicinal value, etc.

Inactive Publication Date: 2013-09-18
ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the low solubility of neogambogic acid in water, it affects its medicinal value to a certain extent.
A comprehensive search of literature found that so far, there are few reports on the structural modification of new gambogic acid, and there are no reports on new gambogic acid derivatives with high activity and low toxicity

Method used

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  • Neogambogic acid derivative, preparation method thereof and pharmaceutical application
  • Neogambogic acid derivative, preparation method thereof and pharmaceutical application
  • Neogambogic acid derivative, preparation method thereof and pharmaceutical application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0161] N, N-dimethyl new gambogic amide (I 1 )Synthesis

[0162] In a dry 25 mL round bottom flask were added neogambogic acid (315 mg, 0.5 mmol), DMAP (6 mg, 0.5 mmol), dimethylamine (0.1 mL), dissolved in 10 mL of dichloromethane. EDCI (115 g, 0.6 mmol) was slowly added dropwise in an ice bath, and the reaction was stirred at room temperature after the drop was completed. The reaction progress was detected by TLC, and the reaction was complete after 24 h. Suction filtration, the filtrate was concentrated, and separated by silica gel column chromatography. Concentrate under reduced pressure and dry to obtain 256 mg of yellow wax. Yield: 78%. IR (KBr, cm -1 ): 1117, 1172, 1216, 1453, 1582, 1630, 1645, 1740, 2858, 2974, 3063, 3430. ESI-MS m / z: 658 [M+H] + ; 1 H NMR (CDCl 3 , 300Hz, δ): 12.86 (1H, s, 6-OH), 7.43 (1H, d, J=6.9Hz, H-10), 5.72 (1H, t, J=7.1Hz), 5.14 (1H, t , J=7.0Hz, H-3), 5.05(1H, m, H-37), 5.02(1H, m, H-32), 3.56(1H, s), 3.40(1H, t, J=4.6, 6.7Hz), 3.23-...

Embodiment 2

[0164] N, N-diethyl neogambogic amide (I 2 )Synthesis

[0165] In a dry 25 mL round bottom flask were added neogambogic acid (315 mg, 0.5 mmol), DMAP (6 mg, 0.5 mmol), diethylamine (0.1 mL), dissolved in 10 mL of dichloromethane. EDCI (115 g, 0.6 mmol) was slowly added dropwise in an ice bath, and the reaction was stirred at room temperature after the drop was completed. The reaction progress was detected by TLC, and the reaction was complete after 24 h. Suction filtration, the filtrate was concentrated, and separated by silica gel column chromatography. Concentrate under reduced pressure and dry to obtain 277mg of yellow wax. Yield: 81%. IR (KBr, cm -1 ): 1117, 1172, 1216, 1453, 1562, 1629, 1648, 1738, 2832, 2965, 3060, 3425. ESI-MS m / z: 686 [M+H] + ; 1 H NMR (CDCl 3 , 300Hz, δ): 12.85 (1H, s, 6-OH), 7.43 (1H, d, J=6.9Hz, H-10), 5.72 (1H, t, J=7.1Hz), 5.14 (1H, t , J=7.0Hz, H-3), 5.05(1H, m, H-37), 5.01(1H, m, H-32), 3.56(1H, s), 3.40(1H, t, J=4.6, 6.7Hz), 3.23-3.36...

Embodiment 3

[0167] Neogamboylglycine (II 1 )Synthesis

[0168] Add neogambogic acid (315mg, 0.5mmoL), glycine methyl ester hydrochloride (75mg, 0.6mmol), DMAP (6mg, 0.5mmol) into a dry 25mL round bottom flask, and dissolve in 10mL of dichloromethane. Slowly add EDCI (115 g, 0.6 mmol) dropwise under ice bath, remove the ice bath after the drop, continue to stir at room temperature, and detect the reaction progress by TLC. After the reaction was completed, it was filtered with suction, and the filtrate was concentrated and subjected to column chromatography to obtain an orange-yellow wax. Dissolve with acetone, add 4% NaOH solution dropwise until the pH of the reaction solution reaches 11, stir the reaction at room temperature, and detect by TLC. After the reaction was completed, 10% hydrochloric acid was added to adjust the pH to 7, concentrated under reduced pressure, the residue was added with appropriate amount of water, and extracted with EtOAc. The organic layer was dried over anh...

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Abstract

The invention relates to the field of pharmaceutical chemistry and pharmacotherapeutics, and in particular relates to a neogambogic acid derivative, as well as a preparation method and a pharmaceutical application thereof. The neogambogic acid derivative has an anti-tumor function and can be used for preparing anti-tumor pharmaceuticals. The invention further relates to the preparation method of the neogambogic acid derivative.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to new gambogic acid derivatives, their preparation methods and their application in pharmacy. The compounds have antitumor effects and can be used for preparing antitumor drugs. The invention also relates to processes for the preparation of such compounds. Background technique [0002] Cancer is currently one of the main killers that endanger human health. In recent years, its incidence has been on the rise, and the number of deaths has increased year by year. Although a variety of anti-tumor drugs are available clinically, due to the complexity of tumor etiology, drug resistance of tumors, and side effects of anti-tumor drugs, the existing drugs still cannot meet the needs of treatment. Therefore, finding new anti-tumor drugs with high drug efficacy, strong targeting, and less toxic and side effects has become a top priority for drug researchers. [...

Claims

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Application Information

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IPC IPC(8): C07D493/10A61K31/352A61K31/453A61K31/5377A61K31/496A61P35/00A61P35/02
Inventor 何黎琴胡钟王效山
Owner ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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