Thymopentin modified by heterocyclic carboxylic acid, its preparation, antitumor effect and application

A technology of heterocyclic carboxylic acid and thymus, which is applied in the direction of antineoplastic drugs, peptide preparation methods, medical preparations containing active ingredients, etc., and can solve problems such as high toxicity and unsatisfactory curative effect

Inactive Publication Date: 2016-08-24
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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  • Thymopentin modified by heterocyclic carboxylic acid, its preparation, antitumor effect and application
  • Thymopentin modified by heterocyclic carboxylic acid, its preparation, antitumor effect and application
  • Thymopentin modified by heterocyclic carboxylic acid, its preparation, antitumor effect and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1 prepares Boc-Val-Tyr-OBzl (1)

[0073] 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 residue...

Embodiment 2

[0074] Embodiment 2 prepares HCl Val-Tyr-OBzl (2)

[0075] 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

[0076] Example 3 Preparation of Boc-Asp(OBzl)-Val-Tyr-OBzl(3)

[0077] 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 present invention discloses thymopentin modified by heterocyclic carboxylic acid represented by general formula I, wherein RCO 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, disclosed their preparation method, disclosed their anti-tumor cell proliferation activity in vitro, further disclosed their activity of inhibiting tumor weight gain in S180 tumor mice, and clarified their application in the preparation of anti-tumor drugs. RCO‑Arg‑Lys‑Asp‑Val‑Tyr I.

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 3S-1,2,3,4-tetrahydro-β-carboline-3-formyl, β-carboline -3-formyl, 3S-1,2,3,4-tetrahydroisoquinoline-3-formyl, isoquinoline-3-formyl, (1S,3S)-1-methyl-1,2 , 3,4-tetrahydro-β-carboline-3-formyl, 1-methyl-β-carboline-3-formyl and 6S-4,5,6,7-tetrahydro-3H-imidazole[ 4,5-C] pyridine-6-formyl), related to their preparation method, related to their anti-tumor cell proliferation activity in vitro, further related to their activity of inhibiting the tumor body weight gain in S180 tumor mice, and clarified their in vivo Application in the preparation of antitumor 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...

Claims

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Application Information

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Patent Type & Authority Patents(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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