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1, 2, 3-triazole compound and application thereof in preparing indoleamine 2, 3-dioxygenase inhibitor

A dioxygenase and compound technology, applied in the direction of active ingredients of heterocyclic compounds, organic chemistry, drug combination, etc., to achieve the effect of broad application prospects

Inactive Publication Date: 2010-07-28
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] IDO is closely related to the pathogenesis of many diseases, and has been proven to be the target of major diseases such as cancer, Alzheimer's disease, depression, cataract, etc. IDO inhibitors have broad application prospects as drugs, but so far there is no suitable IDO Inhibitors can be marketed as drugs, so finding new and efficient IDO inhibitors has important theoretical significance and application value

Method used

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  • 1, 2, 3-triazole compound and application thereof in preparing indoleamine 2, 3-dioxygenase inhibitor
  • 1, 2, 3-triazole compound and application thereof in preparing indoleamine 2, 3-dioxygenase inhibitor
  • 1, 2, 3-triazole compound and application thereof in preparing indoleamine 2, 3-dioxygenase inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Preparation of 4-phenyl-1H-1,2,3-triazole (compound 1)

[0037]

[0038] To a sealed tube filled with nitrogen, add trans-2,3-dibromo-3-phenylpropanoic acid (1 mmol) and 3 mL of DMF, followed by NaN 3 (4.0mmol), stirred at room temperature for 30min. Then add Xantphos (0.04mmol), Pd 2 (dba) 3 (0.01 mmol), sealed immediately, heated to 105° C. in an oil bath, and continued to heat for 30 h after the temperature was constant to synthesize 4-phenyl-1H-1,2,3-triazole with a yield of 71%. Among them: trans-2,3-dibromo-3-phenylpropionic acid and NaN 3 The molar ratio of trans-2,3-dibromo-3-phenylpropionic acid to Xantphos is 1:0.04; trans-2,3-dibromo-3-phenylpropionic acid to Pd 2 (dba) 3 The molar ratio of the reaction solvent DMF is 1:0.01; the mass ratio of the total volume of the reaction solvent DMF to trans-2,3-dibromo-3-phenylpropionic acid is 3 (mL): 1 (mmoL). The product is a white solid. 1 H NMR (500MHz, CDCl 3 +d 6 -DMSO): δ7.32-7.44 (3H, m),...

Embodiment 2

[0039] Example 2: Preparation of 4-(2-bromophenyl)-1H-1,2,3-triazole (compound 6)

[0040]

[0041] To a sealed tube filled with nitrogen, add trans-2,3-dibromo-3-(2-bromophenyl)propanoic acid (1 mmol) and 3 mL of DMF, followed by NaN 3 (4.0mmol), stirred at room temperature for 30min. Then add Xantphos (0.04mmol), Pd 2 (dba) 3 (0.01mmol), seal it immediately, heat the oil bath to 110°C, continue heating for 36h after the temperature is constant, and synthesize 4-(2-bromophenyl)-1H-1,2,3-triazole with a yield of 55%. Among them: trans-2,3-dibromo-3-(2-bromophenyl)propionic acid and NaN 3 The molar ratio of trans-2,3-dibromo-3-(2-bromophenyl)propionic acid and Xantphos is 1:0.04; trans-2,3-dibromo-3-( 2-Bromophenyl)propionic acid and Pd 2 (dba) 3 The molar ratio of the reaction solvent DMF is 1:0.01; the molar ratio of the total volume of the reaction solvent DMF to trans-2,3-dibromo-3-(2-bromophenyl)propionic acid is 3 (mL): 1 (mmoL). The product is a white solid. 1...

Embodiment 3

[0042] Example 3: Preparation of 4-(2-chlorophenyl)-1H-1,2,3-triazole (compound 8)

[0043]

[0044] To a sealed tube filled with nitrogen, add trans-2,3-dibromo-3-(2-chlorophenyl)propionic acid (1 mmol) and 3 mL of DMF, followed by NaN 3 (4.0mmol), stirred at room temperature for 30min. Then add Xantphos (0.04mmol), Pd 2 (dba) 3 (0.01mmol), seal it immediately, heat the oil bath to 110°C, continue heating for 36h after the temperature is constant, and synthesize 4-(2-chlorophenyl)-1H-1,2,3-triazole with a yield of 56%. Among them: trans-2,3-dibromo-3-(2-chlorophenyl)propionic acid and NaN 3 The molar ratio of trans-2,3-dibromo-3-(2-chlorophenyl)propionic acid and Xantphos is 1:0.04; trans-2,3-dibromo-3-( 2-Chlorophenyl)propionic acid and Pd 2 (dba) 3 The molar ratio of the reaction solvent DMF is 1:0.01; the molar ratio of the total volume of the reaction solvent DMF to trans-2,3-dibromo-3-(2-chlorophenyl)propionic acid is 3 (mL): 1 (mmoL). The product is a white so...

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Abstract

The invention belongs to the field of pharmaceutical chemistry and relates to a 1, 2, 3-triazole compound, comprising 4-(2-bromophenyl)-1H-1, 2, 3-triazole and 4-(2-chlorphenyl)-1H-1, 2, 3-triazole. The result of an inhibitory activity test of indoleamine 2, 3-dioxygenase indicates that the disclosed 1, 2, 3-triazole compound used as the indoleamine 2, 3-dioxygenase inhibitor has broad prospect of application and can be applied to the treatment of diseases with indoleamine 2, 3-dioxygenase-mediated tryptophan metabolic pathway pathological characteristics, including cancer, AIDS (Acquired Immure Deficiency Syndrome), Alzheimer disease, tristimania, cataract and other critical diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to 1,2,3-triazole compounds and their application in medicine. Specifically related to 1,2,3-triazole compounds and their use in the preparation of indoleamine 2,3-dioxygenase inhibitors Background technique [0002] Indoleamine 2,3-dioxygenase (Indoleamine 2,3-dioxygenase, IDO) is an enzyme containing heme in cells, and it is the only one outside the liver that can catalyze the metabolism of tryptophan to make it along the path of kynurenine The rate-limiting enzyme of the acid pathway breaks down to a series of metabolites including quinolinic acid (MacKenzie, C.R.Et.al. Current Drug Metabolism, 2007, 8:237-244.). [0003] IDO is related to many physiological and pathological processes. Studies on pregnant mouse models have found that syncytiotrophoblast cells and antigen-presenting cells at the maternal-fetal interface can synthesize IDO and that the dynamic changes in IDO expre...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D401/04C07D257/04A61K31/4192A61K31/4439A61K31/41A61P35/00A61P25/28A61P37/02A61P27/12A61P25/22A61P25/24
Inventor 杨青匡春香郑茂发于存静
Owner FUDAN UNIV
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