3S-indoleethyl-6S-polar amino acid modified piperazine-2,5-dione, and synthesis, activity and application thereof

An amino, diketone technology, applied in the field of biomedicine, can solve the problems of unsatisfactory clinical efficacy of tumor chemotherapy and no anti-tumor metastasis effect.

Inactive Publication Date: 2018-12-07
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the existing anti-tumor drugs have no anti-tumor metast...

Method used

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  • 3S-indoleethyl-6S-polar amino acid modified piperazine-2,5-dione, and synthesis, activity and application thereof
  • 3S-indoleethyl-6S-polar amino acid modified piperazine-2,5-dione, and synthesis, activity and application thereof
  • 3S-indoleethyl-6S-polar amino acid modified piperazine-2,5-dione, and synthesis, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 Preparation of Boc-Lys(Cbz)-Trp-OBzl

[0020] Suspend 7.7g (20mmol) of Boc-Lys(Cbz) in 100mL of anhydrous tetrahydrofuran (THF), and add 2.7g (20mmol) of 1-hydroxybenzotriazole (HOBt) to the suspension in an ice bath. And 5.0g (25mmol) of dicyclohexylcarbodiimide (DCC), and then stirred for 30min. After that, 8.0 g (25 mmol) of Trp-OBzl was added. The reaction compound was added dropwise with N-methylmorpholine (NMM) to adjust the pH to 9. The reaction mixture was first stirred under an ice bath for 1 h, and then at room temperature for 12 h. The reaction compound was filtered, the filtrate was concentrated under reduced pressure, and the residue was dissolved in 150 mL of ethyl acetate solution. The resulting ethyl acetate solution was sequentially used with 5% KHSO 4 Wash with aqueous solution 3 times and saturated NaCl aqueous solution 3 times. Anhydrous Na for ethyl acetate layer 2 SO 4 Dry for 12h, filter, and concentrate the filtrate to dryness under re...

Embodiment 2

[0021] Example 2 Preparation of Lys(Cbz)-Trp-OBzl

[0022] 3.8 g (5 mmol) Boc-Lys(Cbz)-Trp-OBzl and 52 mL of hydrogen chloride in ethyl acetate were slowly mixed with stirring in an ice bath. The resulting solution was stirred in an ice bath for 5h. After that, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in 50 mL of anhydrous ethyl acetate, and the resulting solution was concentrated under reduced pressure. This operation was repeated three times. The residue was washed thoroughly with anhydrous ether to obtain 3.45 g (92%) of the title compound as a yellow powder. ESI-MS(m / e):557[M+H] + .

Embodiment 3

[0023] Example 3 Preparation of (3S,6S)-3-(benzyloxycarbonylamino-n-butyl)-6-(indole-3-ethyl)-piperazine-2,5-dione (1)

[0024] 3.45 g (6.2 mmol) Lys(Cbz)-Trp-OBzl was dissolved in 150 mL ethyl acetate. After the obtained solution was washed three times with a 5% aqueous sodium bicarbonate solution, the ethyl acetate solution was stirred at room temperature for 12 hours to allow colorless solids to be analyzed. 1.9 g (55%) of the title compound was filtered off. ESI-MS(m / e):449[M+H] + .

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PUM

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Abstract

The invention discloses (3S,6S)-3-(AA-amino-n-hexanoylamino-n-butyl)-6-(indole-3-ethyl)-piperazine-2,5-dione with a formula which is described in the specification (in the formula, AA is selected fromthe group consisting of L-Asp residues, L-Arg residues, L-Gln residues, L-Glu residues, L-Lys residues, L-Asn residues, L-Ser residues and L-Thr residues). The invention disclose a preparation method, antitumor activity, antitumor metastatic activity and anti-inflammatory activity of the (3S,6S)-3-(AA-amino-n-hexanoylamino-n-butyl)-6-(indole-3-ethyl)-piperazine-2,5-dione. The invention also discloses an application of the (3S,6S)-3-(AA-amino-n-hexanoylamino-n-butyl)-6-(indole-3-ethyl)-piperazine-2,5-dione in preparation of antitumor drugs, antitumor metastatic drugs and anti-inflammatory drugs.

Description

Technical field [0001] The present invention relates to (3S,6S)-3-(AA-amino-hexanoylamino-n-butyl)-6-(indole-3-ethyl)-piperazine-2,5-dione. It relates to their preparation method, their anti-tumor activity, their anti-tumor metastasis activity, and their anti-inflammatory activity. Therefore, the present invention relates to their use in the preparation of anti-tumor drugs, anti-tumor metastasis drugs and anti-inflammatory drugs. Applications. The invention belongs to the field of biomedicine. Background technique [0002] Tumors seriously threaten human health. In addition to the poor prognosis of cancer patients, the concurrent metastasis of tumors further worsens the prognosis of patients. For example, more than 90% of cancer patients died of metastasis. Since the existing anti-tumor drugs have no anti-tumor metastasis effect, the clinical efficacy of tumor chemotherapy is not ideal. The invention of anti-tumor metastasis drugs is an urgent clinical need. Previously, the...

Claims

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Application Information

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IPC IPC(8): C07K5/033C07K1/06A61K38/07A61P35/00A61P29/00
CPCA61K38/00C07K5/021
Inventor 赵明彭师奇吴建辉王玉记桂林张筱宜李姗姗
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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