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Isoflavone derivative modified by acetylaminoacid benzyl ester, preparation method and application thereof

A technology of amino acid benzyl ester and trihydroxy isoflavone, applied in the field of biomedicine, can solve the problem that the anti-tumor activity cannot meet the needs of anti-tumor treatment and the like

Inactive Publication Date: 2009-10-28
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the antitumor activity of 5,7,4'-trihydroxyisoflavones cannot meet the needs of antitumor therapy.

Method used

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  • Isoflavone derivative modified by acetylaminoacid benzyl ester, preparation method and application thereof
  • Isoflavone derivative modified by acetylaminoacid benzyl ester, preparation method and application thereof
  • Isoflavone derivative modified by acetylaminoacid benzyl ester, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1 prepares the general method of bromoacetyl amino acid benzyl ester

[0017] Dissolve 0.005mol of bromoacetic acid with 60ml of anhydrous THF in a 100ml eggplant bottle, add 0.005mol of DCC under ice-cooling, wait until the reaction is complete (about 30 minutes), add 0.005mol of AA-OBzl, add NMM to adjust pH-8~9 , TLC to monitor the reaction, the reaction was terminated after the disappearance of the AA-OBzl raw material, filtered, and the filtrate was concentrated to dryness under reduced pressure. The obtained residue was dissolved in 100 mL of ethyl acetate, placed in a 250 mL separatory funnel, washed successively with saturated aqueous sodium bicarbonate (30 mL×3), saturated aqueous sodium chloride (30 mL×3), 5% potassium bisulfate Wash with aqueous solution (30mL×3), wash with saturated aqueous sodium chloride solution (30mL×3), wash with saturated aqueous sodium bicarbonate solution (30mL×3), and wash with saturated aqueous sodium chloride solution (...

Embodiment 2

[0018] Embodiment 2 prepares bromoacetylglycine benzyl ester

[0019] According to the general method of Example 1, 585 mg (yield 68.9%) of benzyl bromoacetylglycine was obtained as a colorless solid with 1 g of Tos·Gly-OBzl. ESI + -MS(m / z)310[M+H+Na] + .

Embodiment 3

[0020] Embodiment 3 prepares bromoacetylalanine benzyl ester

[0021] According to the general method of Example 1, 455 mg (yield 53.2%) of benzyl bromoacetylalanine was obtained as a colorless solid with 1 g of Tos·Ala-OBzl. ESI + -MS(m / z)324[M+H+Na] + .

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Abstract

The invention discloses an isoflavone derivative modified by acetylaminoacid benzyl ester of a general formula Ia-q, in which R1, R2 and R3 are all CH2CO-AA-OBzl or both R1 and R2 are all CH2CO-AA-OBzl, while R3 is H, wherein the AA in the CH2CO-AA-OBzl is selected from glycin, lactamine, phenyl alanine, tryptophan, isoleucine, leucine, valine, aspartic acid and glutamic acid. The invention also discloses a preparation method of the isoflavone derivative modified by the acetylaminoacid benzyl ester of the general formula Ia-q. The invention adopts an S180 mouse model to evaluate the antitumor effects of the isoflavone derivative modified by the acetylaminoacid benzyl ester of the general formula Ia-q, thus indicating that the isoflavone derivative has excellent antitumor activity and can be used as an antitumor agent.

Description

technical field [0001] The invention relates to a series of isoflavone derivatives modified by acetylamino acid benzyl ester and the preparation method thereof, and further relates to their application in the preparation of antitumor drugs. The invention belongs to the field of biomedicine. Background technique [0002] Malignant tumor is a common and frequently-occurring disease that seriously threatens human health. The mortality rate of human beings caused by malignant tumors is the second highest among all diseases, second only to cardiovascular and cerebrovascular diseases. Tumor treatments include surgery, radiation therapy, and drug therapy (chemotherapy). At present, chemotherapy is still the main means of clinical treatment of tumors. Searching for antitumor drugs is one of the hot spots in new drug research. [0003] 5,7,4′-Trihydroxyisoflavone is a known natural product with antitumor activity, and its antitumor effect is through cytotoxicity to tumor cells, in...

Claims

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Application Information

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IPC IPC(8): C07D311/36C07D405/14A61K31/352A61K31/405A61P35/00
Inventor 赵明彭师奇李一帆
Owner PEKING UNIV
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