3-nitro-8-ethyoxyl-2H-chromene compound and preparation method and application thereof

A technology of benzopyran and ethoxy, which is applied in the field of medicine, can solve the problems of drug resistance target specificity and broad spectrum, and achieve the effect of increasing the expression level

Inactive Publication Date: 2012-07-18
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, such drugs also face some new problems in clinical practice, including drug resistance, target specificity and broad-spectrum, clinical patient selection, efficacy evaluation and personalized medicine, etc.

Method used

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  • 3-nitro-8-ethyoxyl-2H-chromene compound and preparation method and application thereof
  • 3-nitro-8-ethyoxyl-2H-chromene compound and preparation method and application thereof
  • 3-nitro-8-ethyoxyl-2H-chromene compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Preparation of 3-nitro-8-ethoxy-2H-benzopyran (YL201211)

[0045] 3-Ethoxy salicylaldehyde (16.6 g, 100 mmol) was dissolved in 800 ml of toluene, dibutylamine (12.9 g, 100 mmol), phthalic anhydride (29.6 g, 200 mmol) were added ), heated to reflux, nitroethanol (11.8 g, 130 mmol) was added 13 times within 12 hours, and the reaction was continued for 24 hours; the solvent was evaporated, and the compound YL201211 (14.2 g) was obtained by column chromatography.

Embodiment 2

[0046] Example 2: Preparation of 3-nitro-6-bromo-8-ethoxy-2H-benzopyran (YL201212)

[0047] 5-Bromo-3-ethoxy salicylaldehyde (24.5 g, 100 mmol) was dissolved in 800 ml of toluene, di-n-butylamine (12.9 g, 100 mmol), phthalic anhydride (29.6 g, 200 mmol), heated to reflux, added nitroethanol (11.8 g, 130 mmol) in 13 times within 12 hours, continued the reaction for 24 hours, evaporated the solvent, and obtained compound YL201212 (17.1 g) by column chromatography.

Embodiment 3

[0048] Example 3: Inhibition by 3-nitro-8-ethoxy-2H-benzopyran (YL201211) and 3-nitro-6-bromo-8-ethoxy-2H-benzopyran (YL201212) Proliferation assay of malignant myeloma and leukemia cells

[0049] Explanation of terms:

[0050] MTT: 3-(4,5-dimethylthiazole-2)-2,5-diphenyltetrazolium bromide, trade name: thiazolium blue; DMSO: dimethylsulfoxide.

[0051] Test materials and methods:

[0052] Experimental materials: LP1 cells, OPM-2 cells, K562 cells, Jurkat cells, 96-well plate, MTT, 10% DMSO (volume ratio).

[0053] LP1 cells, OPM-2 cells, K562 cells, and Jurkat cells were all provided by Tang Zhongying Blood Center of Soochow University.

[0054] The specific operation is as follows:

[0055] The myeloma cell line LP1, the myeloma cell line OPM-2, the leukemia cell line K562, and the leukemia cell line Jurkat were evenly inoculated in a 96-well plate at a density of 10,000 cells / ml, and 100 microliters of cell. The cell culture environment is 37°C, 5% carbon dioxide (vol...

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Abstract

The invention belongs to the technical field of medicine, and discloses a 3-nitro-8-ethyoxyl-2H-chromene compound (formula III) and a preparation method thereof. The invention further discloses an application of the compound to preparation of an antitumor medicament. In the formula III, R is H or Br.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to 3-nitro-8-ethoxy-2H-benzopyran compounds, their preparation method and application. Background technique [0002] Cancer is a common and frequently-occurring disease that seriously threatens human health. Statistics in the past ten years show that the mortality rate of human beings due to cancer is second only to cardiovascular and cerebrovascular diseases, and the incidence of cancer is also increasing year by year. Drugs for the treatment of clinical tumors are currently divided into traditional cytotoxic drugs and new molecular targeted drugs. The former mainly acts on DNA, RNA, tubulin and other common components that are critical to cell life and death, resulting in low selectivity and high toxicity; while the latter mainly acts on the regulation of cell proliferation and growth that is very different in normal cells and tumor cells. Key molecules and their sig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/64A61K31/352A61P35/00A61P35/02
Inventor 刘兆鹏尹树强毛新良
Owner SHANDONG UNIV
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