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Triazole compounds as well as preparation method and application thereof

A technology of triazoles and compounds, which is applied in the field of anti-AI-2 quorum sensing drugs, can solve the problem that research results are rarely reported, etc.

Inactive Publication Date: 2011-10-19
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the crystal structures of the AI-2 quorum sensing receptor protein LuxP and the complex LuxPQ have been resolved successively, so far there are few reports on drug design for this target

Method used

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  • Triazole compounds as well as preparation method and application thereof
  • Triazole compounds as well as preparation method and application thereof
  • Triazole compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0067] Example 1: Preparation of N-2,4-dichlorophenyl-4-(N-benzylmethylamino)-1H-1,2,3-triazole hydrochloride (5a):

[0068] Preparation of 2,4-dichloroazidobenzene (2a):

[0069] 30 milliliters of water and 30 milliliters of concentrated hydrochloric acid were added to a 250 mL three-necked flask, 1.7 g (10.49 mmol) of 2,4-dichloroaniline was added, the temperature was cooled to -3°C in an ice-salt bath, and 1.39 g of sodium nitrite ( 20.14mmol) and 10 ml of water solution, the solution gradually becomes light yellow. After the dropwise addition was completed, the reaction was continued for ten minutes. Prepare a mixed solution of 1.35g (20.17mmol) of sodium azide and 10ml of water, add dropwise with a dropping funnel below 0°C, a large number of bubbles are generated and a white solid is precipitated. The dropwise addition is complete. Yellow-white flocculent precipitates float on the surface. Move to room temperature to continue the reaction for 3h. The reaction soluti...

example 2

[0074] Example 2: Preparation of N-2-methoxyphenyl-4-(N-benzylmethylamino)-1H-1,2,3-triazole hydrochloride (5b):

[0075] Preparation of 2-methoxybenzeneazido (2b):

[0076] Add 25mL of water and 25mL of concentrated hydrochloric acid in a 250ml three-necked flask, drop in 1.83g (15mmol) of 2-methoxyaniline, cool to -3°C in an ice-salt bath, the solution is yellow, then add dropwise 1.84g of sodium nitrite ( 27mmol) of 10mL aqueous solution, the color of the solution deepened and turned brown, after the dropwise addition was completed, the reaction was continued for ten minutes. Below 0°C, add 1.78g (27mmol) NaN dropwise 3 With 15mL of aqueous solution, below 0°C, a large number of bubbles will be generated and a white solid will be precipitated. The dropwise addition is complete. Yellow-white flocculent precipitates float on the surface. Move to room temperature to continue the reaction for 3h. Post-processing: The reaction solution was extracted with ethyl acetate 3×30m...

example 3

[0081] Example 3: Preparation of N-2,4-dichlorophenyl-4-(N-2-fluorobenzylmethylamino)-1H-1,2,3-triazole hydrochloride (5e):

[0082] Preparation of 2,4-dichloroazidobenzene (2a):

[0083] 30 milliliters of water and 30 milliliters of concentrated hydrochloric acid were added to a 250 mL three-necked flask, 1.7 g (10.49 mmol) of 2,4-dichloroaniline was added, the temperature was cooled to -3°C in an ice-salt bath, and 1.39 g of sodium nitrite ( 20.14mmol) and 10 ml of water solution, the solution gradually becomes pale yellow. After the dropwise addition was completed, the reaction was continued for ten minutes. Prepare a mixed solution of 1.35g (20.17mmol) of sodium azide and 10ml of water, add dropwise with a dropping funnel below 0°C, a large number of bubbles are generated and a white solid is precipitated. The dropwise addition is complete. Yellow-white flocculent precipitates float on the surface. Move to room temperature to continue the reaction for 3h. The reaction...

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Abstract

The invention discloses triazole compounds and a preparation method thereof as well as application of the triazole compounds in pharmacy. The compounds or pharmaceutical salts thereof are shown in formulas (I) and (II). In the formulas, Ar1 is various substituted aromatic rings, preferably, phenyl, 4-methyl phenyl or 2-fluorophenyl; Ar2 is various substituted aromatic ring substituent groups, preferably, 2,4-dichlorphenyl, 2-methoxy phenyl, 3-methoxy phenyl, or 4-methoxy phenyl; and Ar3 is various substituted aromatic rings, preferably, pyridine or 4-chlorophenyl furan. The compounds can be used for medicaments capable of resisting AI-2 group sensing. The preparation method of the compounds has the advantages of mile reaction condition and cheap and available raw material, and is simple to operate and post-treat.

Description

technical field [0001] The invention relates to triazole derivatives, a preparation method and an application as an AI-2 quorum sensing inhibitor, and belongs to the technical field of anti-AI-2 quorum sensing drugs. Background technique [0002] Bacterial quorum sensing (Quorum Sensing) is a regulatory mechanism of bacterial population behavior that has been focused on in recent years, that is, bacteria can secrete one or more signal molecules called autoinducers, and then sense these autoinducers. Inducers are used to judge the density of the bacterial population and the changes in the surrounding environment. When the number of the bacterial population reaches a certain threshold (quorum, colony or colony number), the corresponding series of gene expression is activated to regulate the colony behavior of the bacteria [Waters, C.M.; Bassler, B.L. Quorum sensing: Cell-to-cell communication in bacteria. Annu. Rev. Cell. Dev. Biol. 2005, 21, 319-346]. At present, according t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06A61K31/4192A61P31/04
Inventor 李敏勇杜吕佩朱鹏
Owner SHANDONG UNIV