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Saturated fatty chain amine His-Gly-AA tripeptide amide, synthetic method and application thereof

A technology of his-gly-aa and aliphatic chain amine, which is applied in the field of biomedicine, can solve the problems of poor water solubility of cyclosporin A, unsatisfactory dosage form or curative effect, strong nephrotoxicity, etc., and achieve excellent immunosuppressive effect

Inactive Publication Date: 2010-12-01
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the extremely poor water solubility and strong nephrotoxicity of cyclosporin A, neither the dosage form nor the curative effect is satisfactory

Method used

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  • Saturated fatty chain amine His-Gly-AA tripeptide amide, synthetic method and application thereof
  • Saturated fatty chain amine His-Gly-AA tripeptide amide, synthetic method and application thereof
  • Saturated fatty chain amine His-Gly-AA tripeptide amide, synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Preparation of Boc-Glu(OBzl)-NHCH 2 (CH 2 ) 6 CH 3

[0040] 1.00g (2.96mmol) Boc-Glu (OBzl) was dissolved in 20ml of anhydrous THF, and 0.39g (2.96mmol) N-hydroxybenzotriazole (HOBt) was added to the resulting solution under ice cooling, and completely dissolve. After 10 minutes 0.74 g (3.55 mmol) of dicyclohexylcarbodiimide (DCC) were added. The reaction liquid (I) was obtained. Put 0.39g (2.96mmol) fatty amine CH under ice bath 3 (CH 2 ) 6 CH 2 NH 2 Suspend in 20ml of anhydrous THF, then add 1ml of N-methylmorpholine (NMM) to adjust the pH to 8-9. Stir for 35 minutes to obtain reaction solution (II). The reaction solution (I) was added to the reaction solution (II) under ice cooling, first stirred under ice cooling for 1 h, and then stirred at room temperature for 12 h, TLC (chloroform / methylamine, 10:1) showed that Boc-Glu (Z) disappeared. Dicyclohexylurea (DCU) was filtered off and THF was removed under reduced pressure. The residue was disso...

Embodiment 2

[0041] Example 2 Preparation of Boc-Glu(OBzl)-NHCH 2 (CH 2 ) 8 CH 3

[0042] According to the method for embodiment 1 by 1.00g (2.96mmol) Boc-Glu (OBzl) and 0.46g (2.96mmol) CH 3 (CH 2 ) 8 CH 2 NH 2 1.35 g (96%) of the title compound were obtained as a colorless solid. ESI-MS(m / z): 477[M+H] + , [α] 20 D =-4.1 (c=1.0, CH 3 OH).

Embodiment 3

[0043] Example 3 Preparation of Boc-Glu(OBzl)-NHCH 2 (CH 2 ) 10 CH 3

[0044] According to the method of embodiment 1 by 1.00g (2.96mmol) Boc-Glu (OBzl) and 0.55g (2.96mmol) CH 3 (CH 2 ) 10 CH 2 NH 2 1.45 g (97%) of the title compound were obtained as a colorless solid. ESI-MS(m / z): 505[M+H] + , [α] 20 D =-3.4 (c=1.0, CH 3 OH).

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Abstract

The invention relates to 12 kinds of saturated fatty chain amine His-Gly-AA tripeptide amide conjugates with immunosuppressive activity in a general formula His-Gly-AA-NH-CH2-(CH2)nCH3 I, wherein AA stands for Glu or Lys, and n is equal to 6, 8 ,10, 12, 14 or 16 in the saturated fatty chain amine. The invention also relates to a preparation method and the application of the conjugates as an immunosuppressant. An experimental result of the saturated fatty chain amine His-Gly-AA tripeptide amide for the inhibition effects of splenic lymphocyte mitogen proliferation reaction and macrophage phagocytosis activity indicates that the conjugates of the invention have excellent immunosuppressive action and can be clinically used as an immunosuppressant.

Description

technical field [0001] The present invention relates to saturated fatty chain amine tripeptide esters, in particular to a series of saturated fatty chain amine His-Gly-AA tripeptide amides with immunosuppressive activity, and also to the preparation method of these saturated fatty chain amine tripeptide esters and their use as immune The application of the inhibitor belongs to the field of biomedicine. Background technique [0002] According to statistics, by the end of 2002, a total of 935,792 cases of various organ transplants had been performed in the world, including 585,877 cases of kidney transplants, 112,153 cases of liver transplants, and 66,559 cases of heart transplants. In addition, pancreas, lung, small intestine and other organ transplants, as well as multi-organ transplants such as heart-lung, pancreas-kidney, liver-kidney, and liver-intestine, have also been successfully applied in clinical practice. Currently, the 1-year human / kidney survival rate of kidney ...

Claims

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Application Information

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IPC IPC(8): C07K5/097C07K1/06C07K1/02A61K38/06A61P37/06A61K47/42A61K9/107A61K9/127
Inventor 赵明彭师奇赵淑锐
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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