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3R-indolemethyl-6S-Lys modified piperazine-2,5-dione, synthesis, activities and applications thereof

A technology of -d-trp-obzl and indole, which is used in drug combinations, non-central analgesics, antipyretics, etc., can solve the problems of unsatisfactory clinical efficacy of tumor chemotherapy and no anti-tumor metastasis effect.

Inactive Publication Date: 2018-12-11
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, synthesis, activities and applications thereof
  • 3R-indolemethyl-6S-Lys modified piperazine-2,5-dione, synthesis, activities and applications thereof
  • 3R-indolemethyl-6S-Lys modified piperazine-2,5-dione, synthesis, activities and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1 prepares D-Boc-Lys(Cbz)-L-Trp-OBzl

[0019] 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

[0020] Embodiment 2 prepares D-Lys(Cbz)-L-Trp-OBzl

[0021] 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

[0022] Example 3 Preparation of (3R,6S)-3-(benzyloxycarbonylamino-n-butyl)-6-(indole-3-methyl)-piperazine-2,5-dione (1)

[0023] 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-(indol-3-methyl)-piperazine-2,5-dione represented by the following formula, a preparation method, anti-tumor-metastasisactivity and anti-inflammatory activity thereof, such that the present invention discloses applications of the (3R,6S)-3-(Lys-amino-n-hexanoylamino-n-butyl)-6-(indol-3-methyl)-piperazine-2,5-dione inpreparation of anti-tumor-metastasis drugs and anti-inflammatory drugs. The formula is defined in the specification.

Description

technical field [0001] The present invention relates to (3R,6S)-3-(Lys-amino-n-hexanoylamino-n-butyl)-6-(indole-3-methyl)-piperazine-2,5-dione. 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. 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 tumor metastasis. Previously, the inventors had disclosed that diketopiperazines with four c...

Claims

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Application Information

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Patent Type & Authority Applications(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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