Application of 2,3 -dihydrogen-3 -hydroxymethyl- 6- amino- [1,4]- benzoxazine in preparing inhibition apoptosis of vascular endothelial cell and promoting neovascularization medicine

A technology of benzoxazine and vascular endothelium, applied in the field of benzoxazine derivatives

Inactive Publication Date: 2007-12-12
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the search by authoritative organizations, 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine, a benzoxazine derivative, can inhibit the apoptosis of vascular endothelial cells and the role in promoting angiogenesis has not been reported at home and abroad

Method used

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  • Application of 2,3 -dihydrogen-3 -hydroxymethyl- 6- amino- [1,4]- benzoxazine in preparing inhibition apoptosis of vascular endothelial cell and promoting neovascularization medicine
  • Application of 2,3 -dihydrogen-3 -hydroxymethyl- 6- amino- [1,4]- benzoxazine in preparing inhibition apoptosis of vascular endothelial cell and promoting neovascularization medicine
  • Application of 2,3 -dihydrogen-3 -hydroxymethyl- 6- amino- [1,4]- benzoxazine in preparing inhibition apoptosis of vascular endothelial cell and promoting neovascularization medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1 Preparation of 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine

[0063] Add 2,4-dinitrophenoxymethyloxirane (0.480 g, 2 mmol) and acetic acid (1 mL, 17.5 mmol) in EtOH / H2O (v / v=6:1, 100 mL) at reflux temperature Iron powder (0.670 g, 12 mmol) was added to the solution. The reaction mixture was continued to reflux for 120 minutes. Cool to room temperature, adjust pH=8 with saturated Na2CO3 solution, filter with celite, concentrate ethanol and water in the filtrate, and wash the obtained solid with ethanol (10mL×4). ethanol phase with anhydrous MgSO 4 Dry and filter to obtain a crude product; the above crude product is separated by silica gel column chromatography (ethanol as a developing solvent) to obtain 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxane Azine (0.149 g, 42%).

Embodiment 2

[0064] Example 2 Using the MTT method to detect the activity of succinate dehydrogenase in cells, and to measure the survival rate of vascular endothelial cells under the culture conditions in which serum and growth factors were removed

[0065] Human umbilical vein endothelial cells were seeded in 96-well cell culture plates, and the normal group was set up: cultured under normal culture conditions containing serum and growth factors; apoptosis-inducing control group: cultured under culture conditions without serum and growth factors ; Solvent control group: add DMSO to culture under the culture condition of removing serum and growth factors; Experimental group: add 2,3-dihydro-2,3-dihydro- 3-Hydroxymethyl-6-amino-[1,4]-benzoxazine incubation. 37°C, CO 2 After culturing in the incubator for 20 hours, add 0.02ml of 5mg / ml MTT solution, and continue at 37°C, CO 2 Cultivate in the incubator for 4 hours, suck out the incubation solution, add 0.1ml dimethyl sulfoxide (DMSO), and...

Embodiment 3

[0067] Example 3 Detection of angiogenesis in vitro

[0068] According to 4~5×10 4 The density of cells / well, the vascular endothelial cells suspended in M199 basal medium without serum and growth factors were inoculated in 24-well cell culture plates with Matrigel in advance, placed at 37°C, CO 2 Incubate in the incubator for 30 minutes to 60 minutes. Then change the cells in the 24-well culture plate to four different detection culture systems, and place them at 37°C, CO 2 Cultivate in an incubator for 24 hours to 96 hours. At 24 hours, 48 ​​hours, 72 hours and 96 hours respectively, the angiogenesis of vascular endothelial cells on Matrigel was observed under an inverted phase-contrast microscope. in,

[0069] Test culture system 1: Under the culture conditions of removing serum and growth factors, no 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine was added as a control group; 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine at concentrations of 25 μM, 50 μ...

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Abstract

The invention discloses the application of 2, 3-dihydro--3-methylol-6-amino-[1, 4]-benzo-oxazine in preparing medicament for inhibiting blood vessel endothelial cell apoptosis and promoting vascularization. Medicament concentration for effectively inhibiting blood vessel endothelial cell apoptosis caused by sera removing and growth factor is 50-200 mu M.Pharmic concentration for promoting angiogenesis in vitro is 50-100 mu M.Pharmic concentration for promoting angiogenesis in vivo is 200-300 mu M.The inventive 2, 3-dihydro--3-methylol-6-amino-[1, 4]-benzo-oxazine can be used as an effective means for researching molecular mechanism of blood vessel endothelial cell apoptosis vascularization.

Description

technical field [0001] The present invention relates to the use of benzoxazine derivatives, in particular to the use of 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in the preparation of anti-vascular endothelial cell apoptosis and Application in promoting angiogenesis drugs. Background technique [0002] The structural formula of 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine is: [0003] [0004] Molecular formula: C 9 h 12 N 2 o 2 [0005] Molecular weight: 180.2, traits: light yellow solid, melting point: 154-156°C [0006] 2,3-Dihydro-[1,4]-benzoxazine derivatives are very important structural units, which are contained in many natural products and synthetic drugs. [0007] It is known that 2,3-dihydro-2-substituted-[1,4]-benzoxazine derivatives have pharmacological activities such as antibacterial, antithrombotic, bradycardia, and anti-central nervous system (CNS) disorders, such as patent The structures of 2,3-dihydro-2-substituted-[1,4]-ben...

Claims

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Application Information

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IPC IPC(8): A61K31/536A61P9/00
Inventor 苗俊英赵宝祥张尚立赵静程轶喆
Owner SHANDONG UNIV
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