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3S-indolylethyl-6S-aliphatic amino acid-modified piperazidine-2,5-dione and synthesis, activity and application thereof

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

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 metastasis effect, the clinical efficacy of tumor chemotherapy is not ideal

Method used

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  • 3S-indolylethyl-6S-aliphatic amino acid-modified piperazidine-2,5-dione and synthesis, activity and application thereof
  • 3S-indolylethyl-6S-aliphatic amino acid-modified piperazidine-2,5-dione and synthesis, activity and application thereof
  • 3S-indolylethyl-6S-aliphatic amino acid-modified piperazidine-2,5-dione and synthesis, activity and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1 prepares Boc-Lys(Cbz)-Trp-OBzl

[0020] Suspend 7.7g (20mmol) Boc-Lys (Cbz) in 100mL of anhydrous tetrahydrofuran (THF), and add 2.7g (20mmol) 1-hydroxybenzotriazole (HOBt) to the suspension successively under ice-cooling And 5.0g (25mmol) dicyclohexylcarbodiimide (DCC), then stirred for 30min. Afterwards, 8.0 g (25 mmol) Trp-OBzl was added. The reaction compound was added dropwise to N-methylmorpholine (NMM) to adjust the pH to 9. The reaction mixture was first stirred under ice bath for 1 h, and then stirred 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 obtained ethyl acetate solution was sequentially washed with 5% KHSO 4 Wash 3 times with aqueous solution and 3 times with saturated NaCl aqueous solution. Ethyl acetate layer with anhydrous Na 2 SO 4 Dry for 12h, filter, and concentrate the filtrate to dry...

Embodiment 2

[0021] Embodiment 2 prepares Lys(Cbz)-Trp-OBzl

[0022] 3.8 g (5 mmol) Boc-Lys(Cbz)-Trp-OBzl was slowly mixed with 52 mL of hydrogen chloride in ethyl acetate under stirring in an ice bath. The resulting solution was stirred for 5 h in an ice bath. 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 well with anhydrous ether to afford 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-(benzyloxycarbonylbutylamino)-6-(indole-3-ethyl)-piperazine-2,5-dione (1)

[0024] 3.45 g (6.2 mmol) of Lys(Cbz)-Trp-OBzl were dissolved in 150 mL of ethyl acetate. After the obtained solution was washed three times with 5% aqueous sodium bicarbonate solution, the ethyl acetate solution was stirred at room temperature for 12 h to fully separate out the colorless solid. 1.9 g (55%) of the title compound were 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-(indolyl-3-ethyl)-piperazidine-2,5-dione, and a preparation method, antitumor activity, antitumor metastasis activity and anti-inflammatory activity thereof. The compounds are shown in a following formula, wherein AA is L-Ala residues, Gly residues, L-Met residues, L-IIe residues, L-Pro residues, L-Val residues and L-Leu residues. Thus the invention discloses application of the compounds in preparation of antitumor drugs, antitumor metastasis drugs and anti-inflammatory drugs.

Description

technical field [0001] The present invention relates to (3S,6S)-3-(AA-amino-n-hexanoylamino-n-butyl)-6-(indole-3-ethyl)-piperazine-2,5-dione. Related to their preparation method, related to their anti-tumor activity, related to their anti-tumor metastasis activity, and related to their anti-inflammatory activity, thus the present invention relates to their 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. Because the existing anti-tumor drugs have no anti-tumor metastasis effect, the clinical curative effect of tumor chemotherapy is unsatisfactory. It is an urgent clinical need to invent drugs against tu...

Claims

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Application Information

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IPC IPC(8): C07D403/06A61K31/496A61P35/00A61P29/00
CPCC07D403/06
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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