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Anthranilamide compound based on entinostat framework as well as preparation and application of anthranilamide compound

A technology of aminobenzamide and entinostat, applied in the field of medicine, can solve problems such as neutropenia and leukopenia

Active Publication Date: 2021-07-30
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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  • Anthranilamide compound based on entinostat framework as well as preparation and application of anthranilamide compound
  • Anthranilamide compound based on entinostat framework as well as preparation and application of anthranilamide compound
  • Anthranilamide compound based on entinostat framework as well as preparation and application of anthranilamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] pyridin-3-ylmethyl 4-(2-aminobenzamido)benzylcarbamate (compound X5, formula II, m=1, X=N)

[0027] (1) Add 3-pyridinemethanol (Formula 6, X=N, 10 mmol), N,N'-carbonyldiimidazole (CDI, 11 mmol) and tetrahydrofuran (50 mL) into a 100 mL reaction flask, and react at room temperature for 1 h. Add 4-aminobenzylamine (11 mmol), 1,8-diazabicycloundec-7-ene (DBU, 10 mmol) and triethylamine (15 mmol), and react at room temperature for 6 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 pyridin-3-ylmethyl 4-aminobenzylcarbamate (Formula 7, m=1, X=N), with a yield of 90%.

[0028] (2) Add pyridin-3-ylmethyl 4-aminobenzylcarbamate (1 mmol), 2-((tert-butoxycarbonyl)amino)benzoic acid (1.2 mmol) 1-ethyl-(3-dimethylaminopropyl)carbonyl Diimine hydrochloride (EDCl, 1.2 mmol), 1-hydroxybenzotriazole (HOBt, 1.3 mmol) were placed in a 50 ml round bottom flask and re...

Embodiment 2

[0031] pyridin-3-ylmethyl 4-(2-(methylamino)benzamido)benzylcarbamate (compound X6, formula II, m=1, X=N, R 2 =NHCH 3 )

[0032] (1) Add 3-pyridinemethanol (Formula 6, X=N, 10 mmol), N,N'-carbonyldiimidazole (CDI, 11 mmol) and tetrahydrofuran (50 mL) into a 100 mL reaction flask, and react at room temperature for 1 h. Add 4-aminobenzylamine (11 mmol), 1,8-diazabicycloundec-7-ene (DBU, 10 mmol) and triethylamine (15 mmol), and react at room temperature for 6 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 pyridin-3-ylmethyl 4-aminobenzylcarbamate (Formula 7, m=1, X=N), with a yield of 90%.

[0033] (2) Add pyridin-3-ylmethyl 4-aminobenzylcarbamate (1 mmol), N-methylanthracene (1.2 mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCl, 1.2 mmol), 1-hydroxybenzotriazole (HOBt, 1.3 mmol) were placed in a 50 ml round bottom flask and repl...

Embodiment 3

[0035] pyridin-3-ylmethyl 4-(2-(dimethylamino)benzamido)benzylcarbamate (compound X7, formula II, m=1, X=N, R 2 =N(CH 3 ) 2 )

[0036] The raw material N-methylanthracene in step (2) of Example 2 was replaced by 2-(dimethylamino)benzoic acid, and the rest of the steps were prepared in the same way as in Example 2, with a yield of 55%. 1 H NMR (300 MHz, Acetone- d 6 ) δ 12.04 (s, 1H), 8.64 (s, 1H), 8.54 (d, J = 3.8 Hz, 1H), 8.10 (dd, J = 7.8, 1.7 Hz, 1H), 7.82 (d, J =7.8 Hz, 1H), 7.74 (d, J = 8.5 Hz, 2H), 7.56 – 7.48 (m, 1H), 7.46 – 7.35 (m,2H), 7.31 (d, J = 8.4 Hz, 2H), 7.27 – 7.20 (m, 1H), 6.96 (s, 1H), 5.16 (s,2H), 4.33 (d, J = 6.2 Hz, 2H), 2.85 (s, 6H). 13 C NMR (75 MHz, Acetone- d 6 ) δ164.82, 157.14, 153.29, 149.85, 149.66, 139.17, 136.70, 135.61, 134.11,133.09, 131.80, 128.79, 128.72, 124.89, 124.38, 121.20, 120.52, 120.42,64.25, 45.28, 44.82.

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Abstract

The invention provides an anthranilamide compound based on an entinostat framework as well as preparation and application of the anthranilamide compound. The structural formula of the anthranilamide compound based on the entinostat framework is shown in the specification, wherein R is methylamino, dimethylamino, hydroxyl, NH2 or a component represented by a structural formula in the specification, X is equal to C, N, and M is equal to 0 or 1. The anthranilamide compound is determined by an MTT method to have the effect of inhibiting gastric cancer cell proliferation, has remarkable anti-gastric cancer activity, has higher activity than 5-fluorouracil on the cellular level, has lower toxicity, 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 an anthranilamide compound based on an entinostat skeleton 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 death...

Claims

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Application Information

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IPC IPC(8): C07D213/30C07C271/20C07C271/28C07C269/00C07C269/06A61P35/00
CPCC07D213/30C07C271/20C07C271/28C07C269/00C07C269/06A61P35/00Y02A50/30
Inventor 王震石桃张红花卢莹美冯益悦李俊芳
Owner NANHUA UNIV
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