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Gypsogenin derivatives

A technology of carnation soap and derivatives, applied in the field of medicine, can solve the problems of high molecular polarity, reduced bioavailability, low fat solubility and the like

Inactive Publication Date: 2017-10-10
INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, dianthogenin has the characteristics of large molecular weight, high molecular polarity, and low fat solubility, thereby reducing its bioavailability. In recent years, it has been reported in the literature that its structure has been modified, and the obtained derivatives have significant anti-HL- 60. The effect of HT-29, Caco-2, Saos-2, MCF-7, HeLa and other cancer cells, and the bioavailability has been improved
However, most of the reported derivatives are acylation of the 3-hydroxyl group and esterification of the 28-position carboxyl group. There are few reports of modification at the 23-position, and no reports of amide formation at the 28-position.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Preparation of 3β-hydroxy-oleanane-12-ene-23-(2,4-dinitrophenylhydrazone)-28-carboxylic acid (compound 2):

[0065] The dianthin (100mg, 2.12×10 -4 mol) and 2,4-dinitrophenylhydrazine (63mg, 3.18×10 - 4 mol) was dissolved in 5 mL of glacial acetic acid and stirred at room temperature for 4 h. The end point of the reaction was controlled by TLC. After the reaction, 20 mL of distilled water was added, followed by ethyl acetate for extraction (3×10 mL), the extract was washed with water, the organic phases were combined, dried over anhydrous sodium sulfate, and dried under reduced pressure to obtain crude compound 2. The crude product was purified by silica gel column chromatography, and the eluent was chloroform / methanol=100 / 2 (V / V), to obtain 107.35 mg of a yellow powdery solid, with a yield of 77.9%; mp 206-207.1°C; IR(KBr)νmax: 3452 ,3302,3101,2941,2860,2853,1697,1618,1589,1519,1463,1425,1386,1332,1277,1216,1139,1075,958,920,832,712,646,580,526,454cm -1 ; LC / MS (ES...

Embodiment 2

[0067] Preparation of N-[3β-acetoxy-oleanane-12-en-23-aldehyde-28-yl]-piperidine (compound 4a):

[0068] Carnation (94mg, 2.0×10 -4 mol) and DMAP (2.44mg, 2.0×10 -5 mol) was dissolved in 5 mL of pyridine, and acetic anhydride was added with stirring at room temperature, and the end point of the reaction was controlled by TLC. After 24 hours, the reaction was completed, and the reaction liquid was transferred to a mixture of ice and water, a white solid precipitated out, extracted with ethyl acetate (3×10 mL), the extract was washed with water, the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product Compound 3, the crude product was purified by silica gel column chromatography, and the eluent was chloroform / acetone=100 / 1 (V / V) to obtain pure compound 3. Compound 3 (40mg, 7.8×10 -5 mol) was dissolved in 3 mL of dry dichloromethane, and oxalyl chloride (2.0×10 -1 mL, 36×10 -3 mol), after 12h, ...

Embodiment 3

[0070] Preparation of N-[3β-acetoxy-oleanane-12-en-23-aldehyde-28-yl]-morpholine (compound 4b):

[0071] Compound 3 (40mg, 7.8×10 -5 mol) was dissolved in 3mL of dry dichloromethane, and oxalyl chloride (2.0×10-1mL, 2.36×10 -3 mol), after 12h, terminate the reaction, evaporate the solvent to dryness under reduced pressure, add dichloromethane to dissolve, evaporate the solvent to dryness, repeat the operation three times, then add dichloromethane to dissolve, stir at room temperature and add triethylamine successively, adjust the pH to neutral After inactivation, add morpholine (3.52×10 -2 mL, 4.04×10 -4 mol), continue to stir for 8h, and TLC controls the reaction end point. After the reaction, adjust the pH to 3-4 with 2mol / L hydrochloric acid aqueous solution, add saturated aqueous sodium chloride solution, wash the organic phase with water, combine the organic phase, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain the crude compound 4b...

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Abstract

The invention relates to gypsogenin derivatives having a structure shown as formula (I) in the specification or pharmaceutically acceptable salts of the gypsogenin derivatives. The compounds have antitumor activity and have an obvious inhibition effect on human colon cancer LOVO cells and lung cancer A549 cells.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a derivative of natural product cepinogenin or a pharmaceutically acceptable salt thereof, a preparation method and application thereof. Background technique [0002] Gypsogenin (gypsogenin) is also known as cotton root saponin, and its chemical name is 3β-hydroxy-12-ene-23-aldehyde-28-carboxylic acid (3β-Hydroxy-23-oxoolean-12-en-28-oic acid), the molecular formula is C 30 h 46 o 4 , the relative molecular weight is 470.70, and the melting point is 273-274°C. It has anti-cancer, anti-bacterial, anti-obesity, anti-diabetic and other pharmacological effects, and has good medicinal prospects and development value. [0003] The structural formula of carnation: [0004] [0005] Gypsogenin, first isolated from Gypsogenin by Japanese botanist Noboru Kutani, has strong anticancer activity. However, dianthogenin has the characteristics of large molecular weight, hi...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/58A61K31/56A61P35/00
CPCC07J63/008
Inventor 孙敬勇张浩超牟艳玲孙捷王风玲吴忠玉王燕宋乐苓
Owner INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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