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Phosphoryl amino acid stilbene derivative, preparing method and application thereof

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 easy availability of raw materials

Inactive Publication Date: 2009-10-21
SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Phosphoryl amino acid stilbene derivative, preparing method and application thereof
  • Phosphoryl amino acid stilbene derivative, preparing method and application thereof
  • Phosphoryl amino acid stilbene derivative, preparing method and application thereof

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 with 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, and 5 μmol / L, 2.5μmol / L, 8 concentration gradients of 1μmol / L. Three replicate wells were set up for each compound, and a negative control and a positive control were set at the same time, 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...

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Abstract

The invention discloses a phosphoryl amino acid stilbene derivative, a preparing method and an application thereof. The compound has a structure general formula shown in formula I, wherein R1 and R2 are both-OCH3 or-H, and AA1 is amino acid residue. The preparing method comprises the step: carrying out a reaction of 2 isopropoxide phosphoryl amino acids and trans-3,5-dimethoxy-4'-amino-stilbene or trans-4-amino-stilbene in the presence of N, N'-dicyclohexyl carbodiimide and 1-hydroxy-triazole at room temperature for 12-14 hours, the molar ratio of the trans-3,5-dimethoxy-4'-amino-stilbene or the trans-4-amino-stilbene to the 2 isopropoxide phosphoryl amino acids is 1:1-1:1.1, the molar ratio is preferably 1:1.05, and solvents can be tetrahydrofuran or methylene dichloride. The compound has good anti-tumor effect and has important practical values and application prospects in the field of preparing anti-tumor medicaments.

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 Applications(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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