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Phosphorylated amino acid stilbene derivative and its preparation method and application

An aminostilbene, phosphorylated amino acid technology, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve problems such as urgent research, strong side effects and drug resistance, To achieve the effect of simple reaction, inhibition of tumor activity, and correct structure

Inactive Publication Date: 2011-12-07
SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Cancer is a malignant tumor. Cancer has seriously threatened human health and life. The combination of traditional chemotherapy drugs, surgery, and radiotherapy has successfully improved the cure rate of various malignant tumors. However, due to strong side effects and resistance Drug properties, making it urgent to find new drugs

Method used

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  • Phosphorylated amino acid stilbene derivative and its preparation method and application
  • Phosphorylated amino acid stilbene derivative and its preparation method and application
  • Phosphorylated amino acid stilbene derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1. Synthesis of trans 3,5-dimethoxy-4'-N-diisopropoxyphosphorylated amino acid stilbene compound

[0020] Add 2mmol 3,5-dimethoxy-4'-aminostilbene and 10mL dry tetrahydrofuran into a 50mL flask, add 2.1mmol N-phosphorylated amino acid (diisopropoxyphosphorylated amino acid) and 2.1mmol·L -1 HOBt (1-hydroxybenzotriazole) solution, add dropwise a condensing agent 2.1mmol DCC (N,N'-dicyclohexylcarbodiimide) and 5mL dry tetrahydrofuran mixed solution in an ice-water bath, and react overnight at room temperature Filtration, the residue was washed three times with THF (tetrahydrofuran), the filtrate and washings were combined, the solvent was removed by rotary evaporation, and the residue was saturated with NaHCO 3 solution, fully stirred and extracted with chloroform, the combined extracts were sequentially washed with saturated NaHCO 3 solution, citric acid aqueous solution with a mass fraction of 10%, and saturated NaCl solution were washed three times, and anhyd...

Embodiment 2

[0033] Example 2, Synthesis of trans 4-N-diisopropoxyphosphorylated amino acid stilbene compound

[0034] Add 2mmol trans-4-aminostilbene and 10mL dry tetrahydrofuran into a 50mL flask, add 2.1mmol N-phosphorylated amino acid and 2.1mmol·L -1 HOBt (1-hydroxybenzotriazole), dropwise add a condensing agent 2.1mmol DCC (N,N'-dicyclohexylcarbodiimide) and 5mL dry tetrahydrofuran mixed solution in an ice-water bath, react overnight at room temperature and filter , the residue was washed three times with tetrahydrofuran, the filtrate and washings were combined, the solvent was removed by rotary evaporation, and the residue was added with saturated NaHCO 3 solution, fully stirred and extracted with chloroform, and the combined extracts were sequentially washed with saturated NaHCO 3 solution, citric acid solution with a mass fraction of 10%, and saturated NaCl solution were washed three times, dried over anhydrous Na2SO4, filtered, washed, and rotary evaporated to remove chloroform,...

Embodiment 3

[0050] Example 3, MTT method cell proliferation inhibitory activity screening

[0051] Take the CNE1 and CNE2 cells (two human nasopharyngeal carcinoma cell lines) in the logarithmic growth phase, and divide them into 2×10 5 Inoculate in a 96-well plate at a density of 1 / mL, 99 μL / well, at 37°C, 5% CO 2 After culturing in the incubator for 4 hours, the compounds prepared in Examples 1 and 2 of the present invention were added to each well so that the final concentrations were 200 μmol / L, 100 μmol / L, 50 μmol / L, 25 μmol / L, 10 μmol / L, 5 μmol / L, 2.5μmol / L, 8 concentration gradients of 1μmol / L. Three replicate wells were set up for each compound, and both negative and positive controls were set up, wherein, the negative control was 1% methanol solution by volume, and the positive control was resveratrol. After acting for 72 hours, add MTT (5mg / ml) solution, 10μL / well, continue to cultivate for 4-6 hours, centrifuge at 2000rpm, 4°C for 5 minutes, absorb the supernatant, add DMSO,...

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Abstract

The invention discloses a phosphorylated amino acid stilbene derivative, a preparation method and application thereof. The general structural formula of the compound is shown in formula I, wherein R1 and R2 are both -OCH3, or both are -H; AA1 is an amino acid residue. The preparation method provided by the invention is to combine diisopropoxyphosphorylated amino acid with trans 3,5-di Methoxy-4'aminostilbene or trans-4-aminostilbene can be reacted. Wherein, the molar ratio of trans-3,5-dimethoxy-4'aminostilbene or trans-4-aminostilbene to diisopropoxyphosphorylated amino acid is 1:1-1:1.1, Preferably 1:1.05, the reaction temperature is room temperature, and the reaction time is 12-14 hours; the solvent can be tetrahydrofuran or dichloromethane. The compound has good antitumor effect, and has important practical value and application prospect in the field of preparing antitumor drugs. Formula I

Description

technical field [0001] The invention relates to a phosphorylated amino acid stilbene derivative, a preparation method and application thereof. Background technique [0002] Tumor is a common and frequently-occurring disease, among which malignant tumor is the most serious disease that endangers human health. Cancer is a malignant tumor. Cancer has seriously threatened human health and life. The combination of traditional chemotherapy drugs, surgery, and radiotherapy has successfully improved the cure rate of various malignant tumors. However, due to strong side effects and resistance Drug properties, making the search for new drugs urgent. [0003] Resveratrol (Resveratrol) referred to as RES, is a natural compound. It was first discovered as early as 1924, and this compound was found in grapes in 1974. Resveratrol has been found in 72 plants in 21 families and 31 genera. Resveratrol has a variety of biological activities, such as preventing cardiovascular disease, anti-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/22A61K31/664A61P35/00
Inventor 蒋宇扬高春梅刘华臣董爱君
Owner SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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