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Method for synthesizing SAICAR

A technology of amino and imidazole, applied in the field of SAICAR synthesis, to achieve the effect of high yield, high purity of finished product and good stability

Pending Publication Date: 2021-11-05
CHONGQING UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These unfavorable factors have become the key bottlenecks for the large-scale and high-purity synthesis of SAICAR

Method used

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  • Method for synthesizing SAICAR
  • Method for synthesizing SAICAR
  • Method for synthesizing SAICAR

Examples

Experimental program
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Effect test

Embodiment 1

[0054] A synthetic (5-amino-1-((3aR,4R,6R,6aR)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole -4-carbonyl)-L-aspartic acid is prepared according to the following steps:

[0055] (1) (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3, Preparation of 4-diacetate:

[0056] Add inosine (8.04g, 30.0mmol) and 4-(dimethylamino)pyridine (0.37g, 3.0mmol, 0.10eq) into 45mL of dry pyridine, and add acetic anhydride (30.60g, 300mmol, 10 equivalents), then the reaction mixture was stirred at 0°C for 1 hour, and then stirred at room temperature for 5 hours, and the reaction was monitored by LC-MS. After the reaction is complete, quench the reaction with 5 mL of cold methanol, concentrate the obtained crude product into a cold solution of ethyl acetate and n-hexane (20 mL) with a volume ratio of 1:3, stir evenly, filter, and filter the cake with a volume ratio of 1:3 ethyl acetate, n-hexane (5mL), ethyl acetate (5mL), and dried i...

Embodiment 2

[0077] A synthetic (5-amino-1-((3aR,4R,6R,6aR)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole -4-carbonyl)-L-aspartic acid is prepared according to the following steps:

[0078](1) (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3, Preparation of 4-diacetate: Add inosine (8.04g, 30.0mmol) and 4-(dimethylamino)pyridine (0.37g, 3.0mmol, 0.10eq) into 45mL of dry pyridine, dropwise at 0°C Acetic anhydride (30.60 g, 300 mmol, 10 equiv) was added, then the reaction mixture was stirred at 0° C. for 1 hour, warmed to room temperature and stirred for 5 hours, and the reaction was monitored by LC-MS. After the reaction is complete, quench the reaction with 5 mL of cold methanol, concentrate the obtained crude product into a cold solution of ethyl acetate and n-hexane (20 mL) with a volume ratio of 1:3, stir evenly, filter, and filter the cake with a volume ratio of 1:3 ethyl acetate, n-hexane (5mL), ethyl acetate (5mL), and ...

Embodiment 3

[0099] A synthetic (5-amino-1-((3aR,4R,6R,6aR)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole -4-carbonyl)-L-aspartic acid is prepared according to the following steps:

[0100] (1) (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3, Preparation of 4-diacetate: Add inosine (8.04g, 30.0mmol) and 4-(dimethylamino)pyridine (0.37g, 3.0mmol, 0.10eq) into 45mL of dry pyridine, dropwise at 0°C Acetic anhydride (30.60 g, 300 mmol, 10 equiv) was added, then the reaction mixture was stirred at 0° C. for 1 hour, warmed to room temperature and stirred for 5 hours, and the reaction was monitored by LC-MS. After the reaction is complete, quench the reaction with 5 mL of cold methanol, concentrate the obtained crude product into a cold solution of ethyl acetate and n-hexane (20 mL) with a volume ratio of 1:3, stir evenly, filter, and filter the cake with a volume ratio of 1:3 ethyl acetate, n-hexane (5mL), ethyl acetate (5mL), and...

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Abstract

The invention relates to a method for synthesizing SAICAR, which comprises the following steps: by taking 5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-imidazole-4-formamide as a raw material, sequentially preparing 5-amino-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuran[3,4-d][1,3]dioxo-4-yl)-1H-imidazole-4-formamide, 5-amino-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuran[3,4-d][1,3]dioxo-4-yl)-1H-imidazole-4 -carboxylic acid, dibenzyl(5-amino-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuran[3,4-d][1,3]dioxo-4-yl)-1H-imidazole-4-carbonyl)-L-aspartic acid and the like, so as to prepare a finished product with the purity of 99.6%, the impurity of 0.4%, the diastereomeric excess (de) value of 97.3% and the yield of 16.9%.

Description

technical field [0001] The invention relates to the field of chemical industry and pharmacy, in particular to a method for synthesizing SAICAR. Background technique [0002] 5-amino-1-((3aR,4R,6R,6aR)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carbonyl )-L-aspartic acid), usually abbreviated as SAICAR, is an extremely important intermediate metabolite in the de novo purine biosynthesis pathway, composed of 5-amino-1-(5-phospho-D-ribose)imidazole-4-carboxy Acid is converted by SAICAR synthetase. In vivo, normal levels of SAICAR can maintain the necessary state of cell physiological functions, while high levels of SAICAR can act as tumor metabolites that promote tumor growth and survival. In addition, SAICAR has good biological value as a non-invasive diagnostic marker and a chemical mimic with therapeutic significance. Therefore, the research and exploration of the properties of SAICAR has become a hot spot in the fields of physiology and ph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558C07F9/6561C07D493/04C07D473/30C07D405/04
CPCC07F9/65586C07F9/6561C07F9/65616C07D493/04C07D473/30C07D405/04C07B2200/07Y02P20/55
Inventor 方波孟江平李佐洋周昊亿徐志刚陈中祝
Owner CHONGQING UNIV OF ARTS & SCI
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