2, 4-diamido-6-pteridine methyl methylamino aminobenzene benzoyl-Glu-peptide, and compound, activity and application thereof

A technology of pteridylmethyl and methylamino, which is applied in the field of biomedicine and can solve problems such as unsatisfactory activity

Active Publication Date: 2017-12-12
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The inventors were not satisfied with this level of activity

Method used

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  • 2, 4-diamido-6-pteridine methyl methylamino aminobenzene benzoyl-Glu-peptide, and compound, activity and application thereof
  • 2, 4-diamido-6-pteridine methyl methylamino aminobenzene benzoyl-Glu-peptide, and compound, activity and application thereof
  • 2, 4-diamido-6-pteridine methyl methylamino aminobenzene benzoyl-Glu-peptide, and compound, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Example 1 Preparation of Boc-Lys(Z)-Glu(OBzl)-OBzl

[0095] 3.80g (10mmol) Boc-Lys (Z) was dissolved in 20mL of anhydrous tetrahydrofuran (dry THF) in a 250mL reaction flask, and 2.47g (12mmol) of N,N-dicyclohexylcarbodiimide (DCC) was added under ice cooling and 0.67g (5mmol) N-hydroxybenzotriazole (HOBt), stirred and activated for 30min to obtain reaction solution A; in addition, 3.27g HCl Glu(OBzl)-OBzl was dissolved in 50mL reaction flask with 20mL dryTHF, and ice bath Slowly add N-methylmorpholine (NMM) dropwise to adjust the pH value to 8 to obtain a reaction solution B. Under an ice bath, add the reaction solution B to the reaction solution A, slowly add NMM dropwise to adjust the pH value to 9, at room temperature Under stirring reaction 12h, thin layer chromatography TLC (dichloromethane:methanol=15:1) shows that reaction is finished, and reaction solution is filtered, and desolvent is removed by concentration under reduced pressure, and residue is separated by...

Embodiment 2

[0096] Example 2 Preparation of HCl Lys(Z)-Glu(OBzl)-OBzl

[0097] 3.72g (5.40mmol) Boc-Lys(Z)-Glu(OBzl)-OBzl was added to a 250mL reaction flask, dissolved with 25mL of anhydrous ethyl acetate, and 54mL of 4N HCl / EA solution was added under ice cooling, and the reaction was stirred for 1.5 h, thin-layer chromatography TLC (dichloromethane: methanol = 15:1) showed that the reaction was complete, the reaction solution was decompressed to remove the solvent, and anhydrous ether was added to remove the solvent and HCl gas under reduced pressure again to obtain 2.86g (90.0%) The title compound as a white solid. ESI-MS(m / e):590[M+H] + .

Embodiment 3

[0098] Example 3 Preparation of Boc-Glu(OBzl)-Lys(Z)-Glu(OBzl)-OBzl

[0099] According to the method of Example 1, by 1.63g (4.86mmol) Boc-Glu (OBzl), 1.20g (5.83mmol) DCC, 0.67g (2.43mmol) HOBt, and 2.86g (4.86mmol) HCl Lys (Z) -Glu(OBzl)-OBzl afforded 2.30 g (52.3%) of the title compound as a white solid. ESI-MS(m / z):909[M+H] + .

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Abstract

The invention discloses seven N-[(4-(2, 4-diamido-6-pteridine methyl-methylamino)-benzoyl]-Glu-Lys-Glu-R and a preparation thereof, inhibition effect of the N-[(4-(2, 4-diamido-6-pteridine methyl-methylamino)-benzoyl]-Glu-Lys-Glu-R on tumor growth and tumor transfer, and application of the N-[(4-(2, 4-diamido-6-pteridine methyl-methylamino)-benzoyl]-Glu-Lys-Glu-R in preparation of antitumor drugs.

Description

technical field [0001] The present invention relates to seven kinds of N-[(4-(2,4-diamino-6-pteridinylmethyl-methylamino)-benzoyl]-Glu-Lys-Glu-R, and their preparation methods, It relates to their inhibitory effect on tumor growth, so the invention relates to their application in the preparation of antitumor drugs, which belongs to the field of biomedicine. Background technique [0002] Methotrexate is a representative of anti-metabolite anti-tumor drugs, which can effectively inhibit dihydrofolate reductase, interfere with the metabolism of cellular nucleic acids, and thus achieve the purpose of killing tumor cells. At present, it plays an important role in the treatment of various tumors such as acute lymphoblastic leukemia, lymphoma, malignant mole, squamous cell carcinoma, choriocarcinoma, lung cancer, breast cancer, cervical cancer and osteosarcoma. Methotrexate can be taken orally and is well absorbed. It can also be injected intramuscularly, and the plasma concentra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/06A61K31/519A61K47/64A61P35/00A61P35/04
CPCA61K31/519C07K7/06Y02P20/55
Inventor 赵明彭师奇王玉记吴建辉李俊
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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