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Diosgenin derivative and preparation method and application thereof

A technology of diosgenin and derivatives, applied in the field of biomedicine, can solve the problems of late clinical symptoms, hidden onset of cholangiocarcinoma, and poor surgical prognosis

Active Publication Date: 2020-01-03
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the insidious onset of cholangiocarcinoma, early diagnosis is difficult, and clinical symptoms appear late. Epidemiological studies have shown that only 10-15% of patients may be cured by surgery, and many patients are found to be in the late stage, but the postoperative recurrence rate is still high. 50-60%, five-year survival rate is only 30%
At present, the treatment principle of cholangiocarcinoma still adopts the comprehensive treatment plan based on surgical resection, but only less than 1 / 3 of the patients can be surgically resected at the time of diagnosis, and the prognosis of surgery is poor. The effect of combined chemotherapy on locally advanced or metastatic unresectable cholangiocarcinoma not ideal

Method used

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  • Diosgenin derivative and preparation method and application thereof
  • Diosgenin derivative and preparation method and application thereof
  • Diosgenin derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Weigh 4.2g of diosgenin and 0.5g of sodium hydride, dissolve them in 100mL of absolute ethanol and 500mL in a three-necked flask, then add 2.0g of o-fluorobenzyl chloride, stir and freeze to 0°C, keep stirring and react for 72h, TLC (developer : sherwood oil-ethyl acetate (7:3), chromogen: 5% phosphomolybdic acid ethanol solution) detects the whole reaction of diosgenin, steams out ethanol, cools down to room temperature, adds water 50mL, extracts 3 times with dichloromethane (60mL×3), TLC traced the separation and purification process of the reaction and the product, recovered dichloromethane from the extract, and dried the solid at 60°C for 4h to obtain 3.8g of a pale yellow powder. The melting point of the target product: 198.2-199.5°C, 13 C NMR (CDCl 3 ,100MHz)δ150.74,140.05,134.43,130.59,129.77,129.70,122.62,120.63,119.75,87.97,82.70,67.20,66.53,62.24,56.91,50.16,42.54,40.51,40.43,39.18,37.77,37.27,32.78,32.56 , 32.25, 31.91, 30.33, 29.94, 28.86, 21.12, 19.97, 18...

Embodiment 2

[0052]Weigh 4.2g of diosgenin, 1.0g of potassium hydride, dissolve in 100mL of methanol and 500mL in a three-necked flask, then add 2.0g of m-fluorobenzyl chloride, stir and heat at 65°C, keep stirring for 36h, TLC (developer: petroleum Ether-ethyl acetate (7:3), chromogenic agent: 5% phosphomolybdic acid ethanol solution) to detect the whole reaction of diosgenin, steam methanol, cool to room temperature, add water 50mL, extract 3 times with dichloromethane (60mL ×3), TLC traced the separation and purification process of the reaction and the product, recovered dichloromethane from the extract, and dried the solid at 60° C. for 4 hours to obtain 3.5 g of a light yellow powder product. The melting point of the target product: 198.5-199.9°C, 13 C NMR (CDCl 3 ,100MHz)δ152.21,140.01,131.40,130.79,129.55,128.77,123.54,120.65,119.74,87.95,82.64,67.15,66.53,62.19,56.86,50.11,42.50,40.46,40.38,39.13,37.72,37.22,32.73,32.51 , 32.20, 31.86, 30.28, 29.89, 28.81, 21.07, 19.92, 18.50, 15...

Embodiment 3

[0054] Weigh 4.2g of diosgenin and 0.8g of sodium ethoxide and dissolve it in 100mL of n-propanol in a 500mL three-necked flask, then add 2.2g of p-fluorobenzyl bromide, stir and heat to 78.5°C, keep stirring and react for 36h, TLC (developing agent: Petroleum ether-ethyl acetate (7:3), chromogen: 5% phosphomolybdic acid ethanol solution) detects the whole reaction of diosgenin, steams n-propanol, cools down to room temperature, adds water 80mL, extracts with chloroform for 3 (100mL×3), TLC traced the separation and purification process of the reaction and the product, recovered chloroform from the extract, and dried the solid at 60°C for 4 hours to obtain 4.0 g of a pale yellow powder. The melting point of the target product: 198.1-199.9°C, 13 C NMR (CDCl 3 ,100MHz)δ151.79,140.11,135.35,131.65,131.65,122.76,122.76,120.81,119.74,87.97,82.70,67.20,66.53,62.24,56.91,50.16,42.54,40.51,40.43,39.18,37.77,37.27,32.78,32.56 , 32.25, 31.91, 30.33, 29.94, 28.86, 21.12, 19.97, 18.56, ...

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Abstract

The invention provides a diosgenin derivative and a preparation method and application thereof. The diosgenin derivative has a structure as shown in a formula (I), wherein R represents phenyl substituted by a substituent, and the substituent is selected from alkyl, alkoxy and halogen; and the invention further provides pharmaceutical acceptable salt of a compound in the formula (I). The compound provided by the invention has a good inhibitory activity for multiplication of bile duct carcinoma cells and human pancreatic cancer cells, and is obviously superior to 5- fluorouracil clinically applied.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular to a diosgenin derivative and a preparation method and application thereof. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Pancreatic cancer is a common pancreatic tumor. It is a highly malignant tumor of the digestive tract that is difficult to diagnose and treat. The 5-year survival rate is <1%. Pancreatic cancer is one of the malignant tumors with the worst prognosis due to its low diagnosis rate and high surgical mortality rate. At present, the main therapeutic drugs are fluorouracil, doxorubicin, ifosfamide, semustine, paclitaxel, gemcitabine, cisplatin, etc., but the clinica...

Claims

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Application Information

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IPC IPC(8): C07J71/00A61K31/58A61P35/00
CPCA61P35/00C07J71/0005
Inventor 刘玉法王目旋彭立增王继庆井晓琳王磊
Owner SHANDONG NORMAL UNIV
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