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Vorinostat skeleton-based anthranilamide compound as well as preparation and application thereof

A technology of aminobenzamide and vorinostat, which is applied in the field of medicine, can solve the problems of neutropenia and leukopenia, achieve high yield, inhibit the proliferation of gastric cancer cells, and have simple and efficient preparation methods

Active Publication Date: 2021-08-03
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the targets of CDK inhibitors on the market are all CDK4 / 6, which are all aimed at breast cancer, and they have adverse reactions such as neutropenia and leukopenia

Method used

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  • Vorinostat skeleton-based anthranilamide compound as well as preparation and application thereof
  • Vorinostat skeleton-based anthranilamide compound as well as preparation and application thereof
  • Vorinostat skeleton-based anthranilamide compound as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 2-amino-N-(7-oxo-7-(phenylamino)heptyl)benzamide (compound X1, formula I, n=6):

[0026] (1) Add 7-aminoheptanoic acid (Formula 1, n=6, 10 mmol), sodium hydroxide aqueous solution (0.5 N, 11 mmol) and 1,4-dioxane (40 mL) into a 100 mL reaction flask , slowly drop di-tert-butyl dicarbonate (11 mmol) in ice bath, and react at room temperature for 3 h. After the completion of the reaction was monitored by TLC, the solvent was evaporated by rotary evaporation and separated by column chromatography to obtain the product 7-((tert-butoxycarbonyl)amino)heptanoic acid (Formula 2, n=6), with a yield of 90%.

[0027] (2) 7-((tert-butoxycarbonyl)amino)heptanoic acid (1 mmol), aniline (1.2mmol) 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride ( EDCl, 1.2 mmol), 4-dimethylaminopyridine (DMAP, 0.1 mmol) were placed in a 50 ml round bottom flask and replaced with argon. After adding 10ml of dry dichloromethane as a solvent, put it in an ice bath and stir, and added triethyl...

Embodiment 2

[0032] 2-(methylamino)-N-(7-oxo-7-(phenylamino)heptyl)benzamide (compound X2, formula I, n=6, R 1 =NHCH 3 ).

[0033] (1) Add 7-aminoheptanoic acid (Formula 1, n=6, 10 mmol), sodium hydroxide aqueous solution (0.5 N, 11 mmol) and 1,4-dioxane (40 mL) into a 100 mL reaction flask , slowly drop di-tert-butyl dicarbonate (11 mmol) in ice bath, and react at room temperature for 3 h. After the completion of the reaction was monitored by TLC, the solvent was evaporated by rotary evaporation and separated by column chromatography to obtain the product 7-((tert-butoxycarbonyl)amino)heptanoic acid (Formula 2, n=6), with a yield of 90%.

[0034] (2) 7-((tert-butoxycarbonyl)amino)heptanoic acid (1 mmol), aniline (1.2mmol) 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride ( EDCl, 1.2 mmol), 4-dimethylaminopyridine (DMAP, 0.1 mmol) were placed in a 50 ml round bottom flask and replaced with argon. After adding 10ml of dry dichloromethane as a solvent, put it in an ice bath and ...

Embodiment 3

[0038] 2-(dimethylamino)-N-(7-oxo-7-(phenylamino)heptyl)benzamide (compound X3, formula I, n=6, R 1 =N(CH 3 ) 2 . )

[0039] Using the method of Example 2, it was prepared from 2-(dimethylamino)benzoic acid with a yield of 70%. 1 H NMR (400 MHz, CDCl 3 ) δ 9.61 (s, 1H), 8.08 (dd, J = 7.8, 1.6 Hz, 1H), 7.99 (d, J =25.4 Hz, 1H), 7.53 (d, J = 8.0 Hz, 2H), 7.41 – 7.32 (m, 1H), 7.23 (d, J = 9.2Hz, 2H), 7.14 (dd, J = 17.1, 7.9 Hz, 2H), 7.02 (t, J = 7.4 Hz, 1H), 3.40 (q, J = 6.8 Hz, 2H), 2.68 (s, 6H), 2.31 (t, J = 7.4 Hz, 2H), 1.63 (dt, J = 50.4,6.9 Hz, 4H), 1.38 (s, 4H). 13 C NMR (101 MHz, CDCl 3 ) δ 171.86, 166.89, 152.48, 138.62, 132.05, 131.58, 129.10, 127.84, 124.52, 124.15, 120.02, 119.98, 45.55, 39.33, 37.64, 28.85, 2

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Abstract

The invention provides a vorinostat skeleton-based anthranilamide compound as well as preparation and application of the anthranilamide compound. The structural formula of the o-aminobenzamide compound based on a vorinostat skeleton is shown in the specification, wherein n is equal to 1-6, and R is methylamino, dimethylamino, hydroxyl, NH2 or the like. The anthranilamide compound based on the vorinostat skeleton has the effect of inhibiting gastric cancer cell proliferation through MTT method determination, and can be used for preparing anti-gastric cancer drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a vorinostat skeleton-based anthranilamide compound and a preparation method thereof, and also relates to the application of the compound in the preparation of anti-gastric cancer drugs. Background technique [0002] Tumor is the second killer that seriously threatens human life and health after cardiovascular and cerebrovascular diseases. In 2018, there were 18.1 million new cases of cancer worldwide and 9.6 million deaths from it. Among them, the incidence rate of gastric cancer ranks fifth, and the mortality rate ranks third. According to statistics, in 2018, there were 1.03 million new cases of gastric cancer worldwide and 783,000 deaths, which is equivalent to 1 case of gastric cancer in every 12 deaths caused by malignant tumors in the world. As a large gastric cancer country, China accounts for more than 40% of the total number of gastric cancer deaths in th...

Claims

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Application Information

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IPC IPC(8): C07C237/36C07C237/22C07C231/12C07C231/02C07C319/22C07C323/62A61P35/00A61P1/00
CPCC07C237/36C07C237/22C07C323/62A61P35/00A61P1/00
Inventor 王震石桃李俊芳张红花卢莹美冯益悦
Owner NANHUA UNIV
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