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Bile acid-alpha-hydroxyphosphonate derivatives and synthetic method thereof

A technology of hydroxyphosphonate and derivatives, which is applied in drug combinations, steroids, antineoplastic drugs, etc., can solve the problems that have not been reported on cholic acid-α-hydroxyphosphonate derivatives, and achieve excellent targeting Effect of selectivity and antitumor activity, good amphipathicity, easy modification

Inactive Publication Date: 2016-07-27
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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Problems solved by technology

Therefore, the combination of cholic acid and α-aminophosphonate to synthesize new cholic acid-α-aminophosphonate derivatives has been explored, but in the existing literature, no cholic acid-α-hydroxyphosphonic acid has been found so far. Related reports on the synthesis of ester derivatives

Method used

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  • Bile acid-alpha-hydroxyphosphonate derivatives and synthetic method thereof
  • Bile acid-alpha-hydroxyphosphonate derivatives and synthetic method thereof
  • Bile acid-alpha-hydroxyphosphonate derivatives and synthetic method thereof

Examples

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Embodiment 1

[0018] (1) Synthesis of Compound 3: Add 10mmol of Compound 2A (or 2B) to a 50mL round bottom flask, then slowly add 12mmol of Compound 1A (or 1B, 1C) dropwise, stir well, then 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 compound (or 3B ~3J).

[0019] (2) Synthesis of compound 4: 6 mmol of DCC and 1 mmol of DMAP were dissolved in 10 mL of tetrahydrofuran, and set aside for later use. Add 40 mL of dried tetrahydrofuran into a 100 mL round-bottomed flask, then add 5 mmol of 3A compound (or 3B to 3J) and 6 mmol of cholic acid, and stir to dissolve it. Under an ice bath, the catalyst was slowly added dropwise into the round bottom flask. After the dropwise addition, the temperature was raised to 65° ...

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Abstract

The invention belongs to the field of pharmaceutical chemistry and particularly relates to novel bile acid-alpha-hydroxyphosphonate compounds and a preparation method thereof. Bile acid and phosphate ester are taken as raw materials, the bile acid-alpha-hydroxyphosphonate series of derivatives with a structural formula represented in the specification are synthesized, the compounds have good antitumor activity, the HepG2 growth inhibition ratio of part of the compounds is up to 75.84%, and the effect is better than that of a control drug Amonafide. Compared with traditional anti-tumor drugs such as bile acid cisplatin compounds and phosphate ester derivatives, bile acid-alpha-hydroxyphosphonate has better target selectivity and anti-tumor activity.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of novel cholic acid-α-hydroxyphosphonate 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 effe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J51/00A61P35/00
CPCC07J51/00
Inventor 霍萃萌郭深深代本才陈瑨赵永德刘晓莉
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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