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Heterocyclic carboxylic acid-modified thymopentins and their preparation method, anti-tumor effect and use

A technology of heterocyclic carboxylic acid and thymus, applied to inhibit the activity of tumor body weight gain in S180 tumor mice, the application in the preparation of anti-tumor drugs, in vitro anti-tumor cell proliferation activity, thymopentin field, can solve the problem of insufficient curative effect Ideal, high toxicity and other issues

Inactive Publication Date: 2013-12-18
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the unsatisfactory curative effect and high toxicity of anti-tumor drugs in clinical application, many research interests have turned to find new anti-tumor drugs with good curative effect and low toxicity

Method used

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  • Heterocyclic carboxylic acid-modified thymopentins and their preparation method, anti-tumor effect and use
  • Heterocyclic carboxylic acid-modified thymopentins and their preparation method, anti-tumor effect and use
  • Heterocyclic carboxylic acid-modified thymopentins and their preparation method, anti-tumor effect and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Example 1 Preparation of Boc-Val-Tyr-OBzl (1)

[0074] Dissolve 0.434g (2.0mmol) Boc-Val in 15mL of anhydrous THF, and add 0.27g (2.0mmol) N-hydroxybenzotriazole (HOBt) and 0.45g (2.2mmol) dicyclohexyl Carbonyldiimide (DCC). After stirring for 5 minutes, a solution of 0.886 g (2.0 mmol) Tos.Tyr-OBzl in anhydrous THF was added. The reaction mixture was adjusted to pH 8-9 with N-methylmorpholine (NMM), and stirred in ice bath for 8 hours. The reaction was stopped, and the precipitated dicyclohexylurea (DCU) was removed by filtration. The filtrate was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and the resulting solution was successively washed with saturated NaHCO 3 Aqueous solution, saturated 5% KHSO 4 aqueous solution and saturated NaCl aqueous solution. Ethyl acetate layer with anhydrous NaSO 4 Let dry for 2 hours. Filter out NaSO 4 , and the filtrate was concentrated under reduced pressure to remove ethyl acetate. The resi...

Embodiment 2

[0075] Example 2 Preparation of HCl Val-Tyr-OBzl (2)

[0076] Dissolve 0.874g (1.79mmol) (1) in 10mL hydrogen chloride-ethyl acetate (4mol / L) solution, stir at room temperature for 2 hours, TLC detects that the raw material point disappears, remove ethyl acetate under reduced pressure, and add a small amount of ether repeatedly Vacuum under reduced pressure to remove acid gas from the product. Finally, a small amount of ether was added to grind the product into solid powder, which was directly used in the next reaction.

Embodiment 3

[0077] Example 3 Preparation of Boc-Asp(OBzl)-Val-Tyr-OBzl(3)

[0078] 0.578g (1.79mmol) Boc-Asp (OBzl) was dissolved in 15mL anhydrous THF, and 0.240g (1.78mmol) HOBt and 0.401g (1.95mmol) DCC were added under ice cooling. After stirring for 5 minutes, a solution of 0.758 g (1.79 mmol) HCl·Val-Tyr-OBzl (2) in anhydrous THF was added. The reaction mixture was adjusted to pH 8-9 with NMM, and stirred in an ice bath for 8 hours. The reaction was stopped, and the precipitated DCU was removed by filtration. The filtrate was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and the resulting solution was successively washed with saturated NaHCO 3 Aqueous solution, 5% KHSO 4 aqueous solution and saturated NaCl aqueous solution. Ethyl acetate layer with anhydrous NaSO 4 Let dry for 2 hours. Filter out NaSO 4 , and the filtrate was concentrated under reduced pressure to remove ethyl acetate. The residue was separated by column chromatography (CH ...

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Abstract

The invention discloses heterocyclic carboxylic acid-modified thymopentins. The heterocyclic carboxylic acid-modified thymopentins have a general formula I. In the general formula I, RCO represents 1,2,3,4-tetrahydro-beta-carboline-3-formyl, beta-carboline-3-formyl, 1,2,3,4-tetrahydroisoquinol-3-formyl, isoquinol-3-formyl, 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-formyl, 1-methyl-beta-carboline-3-formyl or 4,5,6,7-tetrahydro-3H-imidazo[4,5-C]pyridyl-6-formyl. The invention also discloses a preparation method of the heterocyclic carboxylic acid-modified thymopentins, and in-vitro tumor cell proliferation-resistant activity of the heterocyclic carboxylic acid-modified thymopentins. The invention further discloses heterocyclic carboxylic acid-modified thymopentin activity of inhibiting weight gain of a tumor in a S180 tumor-loading mice, and use of the heterocyclic carboxylic acid-modified thymopentins in preparation of anti-tumor drugs. The general formula I is RCO-Arg-Lys-Asp-Val-Tyr.

Description

technical field [0001] The present invention relates to thymopentin modified by heterocyclic carboxylic acid represented by general formula I (RCO in the formula is 1,2,3,4-tetrahydro-β-carboline-3-formyl, β-carboline-3 -Formyl, 1,2,3,4-tetrahydroisoquinoline-3-formyl, isoquinoline-3-formyl, 1-methyl-1,2,3,4-tetrahydro-β- Carboline-3-formyl, 1-methyl-β-carboline-3-formyl and 4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-formyl ), related to their preparation method, related to their in vitro anti-tumor cell proliferation activity, further related to their activity of inhibiting the tumor body weight gain in S180 tumor mice, and clarified their application in the preparation of anti-tumor drugs. The invention belongs to the field of biomedicine. [0002] RCO-Arg-Lys-Asp-Val-Tyr I Background technique [0003] Malignant tumor is a common disease that seriously threatens human health. The mortality rate of human beings caused by malignant tumors ranks second in all disease ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/06C07K1/02A61K38/08A61P35/00
CPCY02P20/55
Inventor 赵明彭师奇吴建辉王玉记胡西
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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