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Cholic acid-alpha-amino phosphonate derivative and synthesis method thereof

A technology of aminophosphonate and derivatives, which is applied in the field of new cholic acid-α-aminophosphonate compounds and their preparation, and can solve the problems that cholic acid-α-aminophosphonate derivatives have not been seen yet, Achieve excellent targeting selectivity, high yield, and excellent antitumor activity

Inactive Publication Date: 2016-07-06
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the existing literature, there have been no relevant reports on cholic acid-α-aminophosphonate derivatives and their synthesis.

Method used

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  • Cholic acid-alpha-amino phosphonate derivative and synthesis method thereof
  • Cholic acid-alpha-amino phosphonate derivative and synthesis method thereof
  • Cholic acid-alpha-amino phosphonate derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Synthesis of compound 3: Add 10mmol of 2A compound (or 2B compound) in a 50mL round bottom flask, then slowly drop 12mmol of 1A compound (or 1B, 1C compound), after stirring evenly, add 1.15g of Anhydrous Potassium Fluoride. Stir vigorously at room temperature until all the liquid in the flask turns into a white solid, add 30 mL of dichloromethane to dissolve it, filter to remove potassium fluoride, distill under reduced pressure to spin the filtrate to dryness, and recrystallize to obtain intermediate 3A (or 3B~ 3J).

[0027] (2) Synthesis of compound 4: Add 40mL of dry chloroform to a 100mL round bottom flask, add 10mmol of 3A compound or (3B~3F compound), stir to dissolve, then drop in 15mmol of triethylamine as an acid-binding solution, cooled to 0°C; 12mmol of p-toluenesulfonyl chloride was dissolved in 20mL of dry chloroform, slowly added dropwise to the flask, reacted at 0°C for 2h, and finally rose to room temperature, and TLC monitored the reaction progres...

Embodiment 2

[0042] Synthesis of compounds 7A-7L: Dissolve 5 mmol of deoxycholic acid (or cholic acid) in 40 mL of dry tetrahydrofuran, add 10 mmol of N,N-carbonyldiimidazole (CDI), stir for 30 min, and then add 6 mmol of compound 6A (or 6B~6F), add 10 mmol of triethylamine dropwise, and react at 45°C. The reaction process was monitored by TLC. After the reaction was completed, the solvent was removed under reduced pressure, dissolved in ethyl acetate, washed three times with dilute hydrochloric acid, saturated sodium bicarbonate solution, and saturated brine successively, and the organic phase was dried with anhydrous sodium sulfate, filtered, and reduced The solvent was removed under pressure, and column chromatography separated V (ethyl acetate): V (petroleum ether): V (dichloromethane) = 1: 5: 0.1 to obtain white solid compound 7A (or 7B-7L).

[0043] The chemical structure, infrared, and NMR data of some preferred compounds synthesized by the present invention are shown in the followi...

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Abstract

The invention belongs to the field of medicine chemistry and particularly relates to a cholic acid-alpha-amino phosphonate derivative and a preparation method thereof.Cholic acid and phosphate ester serve as raw materials, and the cholic acid-alpha-amino phosphonate derivative with the following general structural formula is synthesized.This kind of compositions has good anti-tumor activity, the human hepatocellular carcinoma cell (HepG2) growth inhibition rate of some compositions is as high as 77.44%, and the advantages of the compositions are better than those of the control drug Amonafide.Please see the general structural formula in the description.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of novel cholic acid-α-aminophosphonate compounds, a preparation method and application thereof. Background technique [0002] Malignant tumor is one of the main diseases that seriously affect human health and threaten human life. Together with cardiovascular and cerebrovascular diseases and accidents, cancer constitutes the top three causes of death in all countries in the world today. Therefore, the World Health Organization (WHO) and the health departments of governments of various countries have listed conquering cancer as a top priority. Currently, there are three main methods of treating tumors: surgery, radiation therapy, and chemotherapy. Among them, chemotherapy is to use drugs to kill cancer cells. The biggest limitation of this method is that it is difficult for drugs to identify normal cells and tumor cells, which has relatively large toxic and side effect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCC07J9/00
Inventor 郭深深霍萃萌陈瑨代本才赵永德刘晓莉
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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