3r-indolemethyl-6s-lys modified piperazine-2,5-dione, its synthesis, activity and application

A technology of -l-trp-obzl and indole, applied in drug combination, non-central analgesics, organic chemistry, etc., can solve the problems of no anti-tumor metastasis effect and unsatisfactory clinical curative effect of tumor chemotherapy

Inactive Publication Date: 2021-02-12
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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  • 3r-indolemethyl-6s-lys modified piperazine-2,5-dione, its synthesis, activity and application
  • 3r-indolemethyl-6s-lys modified piperazine-2,5-dione, its synthesis, activity and application
  • 3r-indolemethyl-6s-lys modified piperazine-2,5-dione, its synthesis, activity and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1 prepares D-Boc-Lys(Cbz)-L-Trp-OBzl

[0021] Add 0.68 g (5.0 mmol) 1-hydroxybenzotriazole (HOBt) and 1.24 g (6.0 mmol) dicyclohexylcarbodiimide (DCC) and stirred for 30 minutes to obtain reaction solution A. 1.47g (5.0mmol) L-Trp-OBzl was dissolved in 20mL dry THF, and N-methylmorpholine (NMM) was added to adjust the pH to 9 to obtain reaction solution B. The reaction solution B was added into the reaction solution A, and reacted at room temperature for 12 hours. TLC (dichloromethane / methanol, 40 / 1) showed that the reaction was complete. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was dissolved in 50 mL of ethyl acetate. The resulting solution was sequentially washed with saturated NaHCO 3 Wash with aqueous solution (25mL×3), wash with saturated NaCl aqueous solution (25mL×3), 5% KHSO 4 Wash with aqueous solution (25mL×3), wash with saturated NaCl aqueous solution (25mL×3), and wash with satura...

Embodiment 2

[0022] Embodiment 2 prepares D-Lys(Cbz)-L-Trp-OBzl

[0023] To 2.62g (4.0mmol) D-Boc-Lys(Cbz)-L-Trp-OBzl under ice-cooling, slowly add 30mL of hydrogen chloride in ethyl acetate solution (4M) and stir for 4 hours, TLC (dichloromethane / methanol, 40 / 1) shows that the reaction is complete. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in 30 mL of anhydrous ethyl acetate. The obtained solution was concentrated under reduced pressure, and the residue was dissolved in 30 mL of anhydrous ethyl acetate. This operation was repeated three times. Add 30 mL of anhydrous diethyl ether to the residue to suspend by means of a sonicator, and remove the diethyl ether after standing still to obtain 2.07 g (93%) of the title compound as a yellow powder. ESI-MS(m / z):557[M+H] + .

Embodiment 3

[0024] Example 3 Preparation of (3R,6S)-3-(benzyloxycarbonylamino-n-butyl)-6-(indole-3-methyl)-piperazine-2,5-dione (1)

[0025] A solution of 1.95g (3.5mmol) D-Lys(Cbz)-L-Trp-OBzl and 50mL ethyl acetate was washed with saturated NaHCO 3 After fully washing with aqueous solution (25 mL×3), the ethyl acetate layer was stirred at 80° C. for 56 hours. TLC (dichloromethane / methanol, 20 / 1) showed the reaction was complete. The reaction mixture was allowed to stand well at room temperature and filtered to afford 0.72 g (46%) of the title compound as a colorless solid. ESI-MS(m / z):449[M+H] + .

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Abstract

The present invention discloses (3R,6S)-3-(Lys-amino n-hexanoylamino n-butyl)-6-(indole-3-methyl)-piperazine-2,5-dione of the following formula. Its preparation method, its anti-tumor metastasis activity and its anti-inflammation activity are disclosed, so the present invention discloses its application in the preparation of anti-tumor metastasis medicine and anti-inflammation medicine.

Description

[0001] field of invention [0002] The present invention relates to (3R,6S)-3-(Lys-amino-n-hexanoylamino-n-butyl)-6-(indole-3-methyl)-piperazine-2,5-dione of the formula. It relates to its preparation method, its anti-tumor metastasis activity, and its anti-inflammatory activity, so the present invention relates to its application in anti-tumor metastasis medicine and anti-inflammatory medicine. The invention belongs to the field of biomedicine. [0003] Background technique [0004] 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 tumor metastasis. Previously, the inventors had disclos...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/06A61P35/04A61P29/00
CPCC07B2200/07C07D403/06
Inventor 赵明彭师奇王玉记吴建辉张可欣
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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