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Trilerium and trilerium marked agmatine and application in biochemistry and medicine research

An agmatine and labeling technology, which is applied in the field of agmatine compounds and its intermediates, can solve the problems of high cost, changes in physicochemical and pharmacological properties, and difficulty in the synthesis of labeled agmatine, and achieve simple synthesis methods and low cost. low effect

Inactive Publication Date: 2006-09-20
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

but 14 C and [ 3 h 8 The synthesis of ]-labeled agmatine is difficult and expensive, and too much tritium labeling will lead to large changes in its physicochemical and pharmacological properties

Method used

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  • Trilerium and trilerium marked agmatine and application in biochemistry and medicine research
  • Trilerium and trilerium marked agmatine and application in biochemistry and medicine research
  • Trilerium and trilerium marked agmatine and application in biochemistry and medicine research

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Example 1: [ 2 h 8 ] Preparation of Agmatine Sulfate:

[0078] 0.119g (1.23mmol) of [ 2 h 8 ]-1,4-Butanediamine and 0.171g (1.23mmol) of S-methylisothiouronium sulfate were dissolved in 15ml of water, reacted at 10-15°C for 5 hours, and then added dropwise sulfuric acid ethanol solution until the pH value was 6-7, the reaction solution was evaporated in vacuo, and the residual solid was recrystallized from 60% methanol to obtain 0.119 g of the title compound, with a yield of 41%.

[0079] 13 C-NMRδppm (D 2 O, DMSO): 158.26, 39.71, 39.50, 28.80, 25.83. MS (FAB) 139.2 (M+H).

Embodiment 2

[0080] Example 2: [ 3 h 4 ] Preparation of Agmatine Sulfate:

[0081] (1) Preparation of 4-amino-2-alkyne-butylguanidine sulfate

[0082] Dissolve 0.190g (2.26mmol) of 2-alkyne-1,4-butanediamine and 0.313g (2.26mmol) of S-methylisothiourea sulfate in 25ml of water, react at 10-15°C for 5 hours, then add dropwise The sulfuric acid ethanol solution was adjusted to a pH of 6-7, the reaction solution was evaporated in a vacuum rotary, and the residual solid was recrystallized with 60% methanol to obtain 0.174 g of 4-amino-2-yne-butylguanidine sulfate, with a yield of 34%.

[0083] 1 H-NMR δppm(D 2 O): 4.08(s, 2H), 3.85(s, 2H). 13 C-NMR δppm (D 2 O, DMSO): 158.35, 82.78, 77.18, 32.29, 30.67. MS(FAB)127.2(M+H), 225.2(M+H+H 2 SO 4 ). Elemental analysis (C 5 h 10 N 4 .H 2 SO 4 ): Calculated: C, 26.78%; H, 5.39%; N, 24.99%, found: C, 26.98%; H, 5.37%; N, 24.69%.

[0084] (2)[ 3 h 4 ] Preparation of Agmatine Sulfate

[0085] Dissolve 0.01g (0.045mmol) of 4-amino-2-yne...

Embodiment 3

[0086] Embodiment 3: [ 2 h 4 ] Preparation of Agmatine Sulfate:

[0087] Dissolve 0.01g (0.045mmol) of 4-amino-2-yne-butylguanidine sulfate in 3ml water, add 0.005g Pd / C catalyst (10%), and react with deuterium gas for 24 hours at normal temperature and pressure , Pd / C was filtered off, the reaction solution was concentrated to about 2ml, and 20ml of absolute ethanol was added to precipitate a solid, which was filtered to obtain the title compound.

[0088] 1 H-NMR δppm(D 2 O): 3.03(s, 2H), 2.82(s, 2H). 13 C-NMR δppm (D 2 O, DMSO): 158.26, 39.92, 39.71, 25.91, 25.44. MS (ESI) 134.2 (M).

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Abstract

This invention relates to deuterium-marked and tritium-marked agmatine and its intermediates, their preparation method and their application the in biochemical mechanism of agmatine and pharmaceutical research.

Description

technical field [0001] The present invention relates to deuterium- and tritium-labeled agmatine compounds and their intermediates, their preparation methods and the application of the compounds and intermediates in the biochemical action mechanism and medical research of agmatine. Background technique [0002] Agmatine is the product of arginine decarboxylation catalyzed by L-arginine decarboxylase (L-ADC), which can be hydrolyzed into putrescine by agmatine or oxidized into arginine by diamine oxidase. [0003] Previous studies have shown that agmatine has many biological effects, mainly in: 1) it can interact with imidazoline receptors and α 2 - Adrenergic receptor binding (G.Li, S.Regunathan, D.J.Reis, Science, 1994, 263, 966-969 and J.E.Piletz, D.N.Chikkala, P.Ernsberger, J.Pharmacol.Exp.Ther., 1995, 272 , 581-587); 2) can dose-dependently block N-methyl-D-aspartate (NMDA) receptors (X.C.Yang, D.J.Reis, J.Pharmacol.Exp.Ther., 1999,288 , 544-549); 3) can regulate the ac...

Claims

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Application Information

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IPC IPC(8): C07C279/12C07C277/08A61K51/00
CPCC07C279/12
Inventor 李松郑志兵何洪夏谢云德陈兰福仲伯华李锦
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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