Saturated fatty chain alcohol His-Gly-AA tripeptide ester, synthetic method and application thereof

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

Inactive Publication Date: 2012-05-23
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 alcohol His-Gly-AA tripeptide ester, synthetic method and application thereof
  • Saturated fatty chain alcohol His-Gly-AA tripeptide ester, synthetic method and application thereof
  • Saturated fatty chain alcohol His-Gly-AA tripeptide ester, synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Preparation of Boc-Glu(OBzl)-OCH 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. 0.39g (2.96mmol) fatty alcohol CH 3 (CH 2 ) 6 CH 2 OH was suspended in 20ml of anhydrous THF, and then 1ml of N-methylmorpholine (NMM) was added 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 / methanol, 10:1) showed that Boc-Glu (OBzl) disappeared. Dicyclohexylurea (DCU) was filtered off and THF was removed under reduced pressure. The residue was dissolved ...

Embodiment 2

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

[0042] According to the method of embodiment 1 by 1.00g (2.96mmol) Boc-Glu (OBzl) and 0.47g (2.96mmol) CH 3 (CH 2 ) 8 CH 2 OH yielded 1.37 g (97%) of the title compound as a colorless oil.

[0043] ESI-MS(m / z): 478[M+H] + , [α] 20 D =-11.6 (c=1.0, CH 3 OH).

Embodiment 3

[0044] Example 3 Preparation of Boc-Glu(OBzl)-OCH 2 (CH 2 ) 10 CH 3

[0045] 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 OH yielded 1.46 g (98%) of the title compound as a colorless oil.

[0046] ESI-MS(m / z): 506[M+H] + , [α] 20 D =-11.5 (c=1.0, CH 3 OH).

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Abstract

The invention relates to 12 saturated fatty chain alcohol His-Gly-AA tripeptide ester conjugates with immunosuppressive activity in a general formula His-Gly-AA-O-CH2-(CH2)nCH3 I, wherein AA stands for Glu or Lys. In saturated fatty chain alcohol, n is equal to 6, 8, 10, 12, 14 or 16. the invention also relates to a preparation method and application of the conjugates as an immunosuppressant. An experimental result of the saturated fatty chain alcohol His-Gly-AA tripeptide ester which has the inhibition effects of splenic lymphocyte mitogen breeder 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 alcohol tripeptide esters, in particular to a series of saturated fatty chain alcohol His-Gly-AA tripeptide esters with immunosuppressive activity, also to the preparation method of these saturated fatty chain alcohol 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 kidne...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/097C07K1/06C07K1/02A61K38/06A61P37/06A61K47/42A61K9/107A61K9/127A61K47/18
CPCY02P20/55
Inventor 赵明彭师奇赵淑锐
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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