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Benzoxazinone derivative and preparation method and application thereof

A technology of benzoxazinone and its derivatives, which is applied in the field of medicinal chemistry, and can solve the problems of inability to realize mass production preparation, limited application, and no economical and efficient synthesis process

Active Publication Date: 2017-09-19
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the harsh reaction conditions, low yield, high cost, heavy metal residues and other defects of the synthetic method mentioned above, it is impossible to realize industrial mass production and preparation, which limits its application in pharmaceutical production.
At present, there is no economical and efficient synthesis process, and there is no relevant mass production preparation process report

Method used

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  • Benzoxazinone derivative and preparation method and application thereof
  • Benzoxazinone derivative and preparation method and application thereof
  • Benzoxazinone derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Synthesis of some compounds of the present invention, including Ia-Ih, taking compound Ia as an example

[0029] Preparation of N-benzyl-2-hydroxy-5-methoxybenzamide:

[0030]

[0031] Dissolve 1 g (5.95 mmol) of 5-methoxysalicylic acid in 30 ml of anhydrous dichloromethane, add 2.14 g (10.7 mmol) of thionyl chloride, 1 drop of N,N-dimethylformamide, After heating up to reflux for 2 hours, cool to room temperature, spin dry to remove solvent, dissolve with anhydrous dichloromethane, add dropwise to anhydrous diethylamine containing 1.85g (17.80mmol) of triethylamine and 0.76g (7.14mmol) of benzylamine. in methyl chloride solution. After the dropwise addition was completed, the mixture was stirred at room temperature for 5 min, and spin-dried to obtain a crude product, 1.27 g of white solid N-benzyl-2-hydroxy-5-methoxybenzamide purified by column chromatography, with a yield of 83%. 1 H NMR (300MHz, DMSO) δ12.62(s, 1H), 7.36-7.32(m, 5H), 7.22(d, J=9.3Hz, 1...

Embodiment 2

[0056] Example 2 Experiment of antitumor activity of compounds Ia-Ih.

[0057] Experimental Materials

[0058] Cell line: human cervical cancer cell HeLa and human breast cancer cell MCF-7; sample: compound Ia-Ih was added with appropriate amount of DMSO to make a concentration of 10 -2 M solution, diluted with culture medium to the corresponding concentration before use.

[0059] experimental method

[0060] Cell digestion and counting, 2.5×10 per well 3 Cells were placed in a 96-well plate with a total volume of 100 μl per well and cultured for 24 hours; the samples to be tested were diluted to an appropriate concentration with medium, 100 μl per well, and three replicate wells were set. After culturing for 72 hours, add 20 μl of 5 mg / ml MTT solution, after incubation for 4 hours, suck out all the liquid in the well, add 100 μl of DMSO, and measure the absorbance with a full-wavelength microplate reader; inhibition rate=(1-average absorbance value of the administration gr...

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PUM

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Abstract

The invention belongs to the field of pharmaceutical chemistry and particularly relates to a benzoxazinone derivative, a preparation method thereof and application thereof in related diseases. The benzoxazinone derivative provided herein has a specific structure shown in formula I or II that is shown in the description. The invention also provides a synthetic method shown in formula I or II and application thereof in related diseases, mainly relating to tumors, cardiovascular diseases, neurodegenerative diseases, metabolic diseases, inflammatory diseases and the like.

Description

technical field [0001] The present invention belongs to the field of medicinal chemistry, and specifically relates to benzoxazinone derivatives represented by formula I or formula II and their preparation methods and their application in related diseases, mainly involving tumors, cardiovascular diseases, neurodegenerative diseases, Metabolic diseases, inflammatory diseases, etc. [0002] Background technique [0003] Tumor is one of the most harmful diseases to human health, seriously affecting people's quality of life. In recent years, chemical drugs, as one of the important means of treating tumors, have made great progress and development. At present, many anti-tumor drugs with different mechanisms of action have been developed, but these drugs show many defects in clinical use, such as poor selectivity, large toxic and side effects, and rapid drug resistance. Therefore, the research and development of new antitumor drugs is particularly important. [0004] Benzoxaz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/26C07D413/04A61K31/536A61P35/00A61P9/00A61P25/28A61P3/00A61P29/00
CPCC07D265/26C07D413/04
Inventor 王进欣高彪赵丽毕晓玲
Owner CHINA PHARM UNIV
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