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Hexacyclic piperazine dione modified with rgd sequence peptide, its preparation, antitumor activity and application

A technology of piperazine and diketone, applied in the application field of preparing antitumor drugs, can solve the problems of expensive treatment price, troubled cancer treatment, multidrug resistance and the like

Active Publication Date: 2022-08-02
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to serious side effects, multidrug resistance after drug treatment and expensive treatment prices, cancer treatment is once again in trouble

Method used

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  • Hexacyclic piperazine dione modified with rgd sequence peptide, its preparation, antitumor activity and application
  • Hexacyclic piperazine dione modified with rgd sequence peptide, its preparation, antitumor activity and application
  • Hexacyclic piperazine dione modified with rgd sequence peptide, its preparation, antitumor activity and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 Preparation of Boc-Arg (NO 2 )-Gly-OBzl

[0024] 1.595 g (5.0 mmol) of Boc-L-Arg (NO 2 ) was dissolved in 20 mL of tetrahydrofuran, then 0.675 g (5.0 mmol) of 1-hydroxybenzotriazole and 1.236 g (6.0 mmol) of dicyclohexylcarbodiimide were added, and the reaction was carried out for 0.5 h. Then 1.854 g (5.5 mmol) Tos·Gly-OBzl was added, and finally the pH of the reaction solution was adjusted to 8 with N-methylmorpholine. The resulting solution was stirred at room temperature for 6h until TLC showed Boc-L-Arg(NO 2 )disappear completely. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The obtained pale yellow oil was dissolved in 60 mL of ethyl acetate. The obtained solution was washed with saturated aqueous sodium bicarbonate solution (20 mL × 3) and saturated aqueous sodium chloride solution (20 mL × 3) successively. , washed with 5% aqueous potassium hydrogen sulfate (20 mL×3), washed with saturated aqueous sodi...

Embodiment 2

[0025] Example 2 Preparation of Boc-Arg (NO 2 )-Gly

[0026] 2.120 g (5.0 mmol) of Boc-Arg (NO 2 )-Gly-OBzl was dissolved in 15 mL of methanol, added with aqueous sodium hydroxide solution (2M) to adjust the pH to 11, and stirred until TLC showed Boc-Arg(NO). 2 )-Gly-OBzl disappeared completely. The reaction solution was first adjusted to neutral pH with saturated aqueous potassium hydrogen sulfate solution, concentrated under reduced pressure, adjusted to pH 2 with saturated aqueous potassium hydrogen sulfate solution, extracted with ethyl acetate (50 mL×3), combined with the ethyl acetate layers and washed with saturated chlorine Washed with aqueous sodium chloride solution (30 mL×3). The ethyl acetate layer was dried over anhydrous sodium sulfate for 12 h, filtered, and the filtrate was concentrated under reduced pressure to obtain 1.542 g (82%) of the title compound as a colorless oily product. ESI-MS(m / e): 375[M-H] - .

Embodiment 3

[0027] Example 3 Preparation of Boc-Asp(OBzl)-Ser-OBzl

[0028] Using the method of Example 1, 2.520 g (92%) of the title compound was obtained as a colorless oil from 1.615 g (5.0 mmol) Boc-L-Asp(OBzl) and 1.271 g (5.5 mmol) L-Ser-OBzl. ESI-MS(m / e):501[M+H] + .

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Abstract

The present invention discloses 9-(CH of the following formula 2 CO-Arg-Gly-Asp-AA)-tetrahydro-β-carboline[3:4]piperazine-2,5-diketopiperidine[4:5]imidazole (where AA is a Ser residue base, Phe residue and Val residue). Their preparation method is disclosed, and their application in the preparation of antitumor drugs is disclosed.

Description

technical field [0001] The present invention relates to 9-(CH of the following formula 2 CO-Arg-Gly-Asp-AA)-tetrahydro-β-carboline[3:4]piperazine-2,5-diketopiperidine[4:5]imidazole. The invention relates to their preparation method and application in the preparation of antitumor drugs. The invention belongs to the field of biomedicine. [0002] Background technique [0003] Tumor has become a common disease that seriously threatens human health. For example, there were approximately 3.929 million new cancer patients in 2015, of which 2.338 million cancer patients died. On average, more than 10,000 people are diagnosed with cancer every day. At present, the clinical application of cancer treatment methods mainly include radiotherapy, chemotherapy, antibody therapy and immunotherapy. However, due to serious side effects, multidrug resistance after drug treatment and expensive treatment prices, the treatment of cancer is once again in trouble. The invention of new anti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/11C07K1/06C07K1/02A61K38/07A61P35/00
CPCC07K5/1019A61P35/00A61K38/00Y02P20/55
Inventor 赵明彭师奇桂琳郝媛萌
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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