Method for improving water solubility of hydroxybenzimidazolyl compound

A technology of hydroxybenzimidazole and compound, which is applied in the field of drug synthesis, and can solve the problems of low solubility, poor water solubility and limited application of hydroxyphenylbenzimidazole compounds

Inactive Publication Date: 2015-04-22
天津药物研究院药业有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The main purpose of the present invention is to provide a kind of simple and easy operation, improve the method for the water solubility of hydroxyphenylbenzimidazoles compound for the poor water-solubi...

Method used

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  • Method for improving water solubility of hydroxybenzimidazolyl compound
  • Method for improving water solubility of hydroxybenzimidazolyl compound
  • Method for improving water solubility of hydroxybenzimidazolyl compound

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Take 1.0 g (8.19 mmol) of salicylaldehyde and 0.85 g (8.19 mmol) of sodium sulfonate, and dissolve them in 25 mL of 95% ethanol to form a solution. At room temperature, it was placed in a 50 mL round bottom flask and reacted for 4 h under magnetic stirring to form a precipitate. Then add 0.89 g (8.19 mmol) of o-phenylenediamine and 25 mL of DMF into the round bottom flask, heat and reflux for 2 h, pour 10 times the amount of water into the solution, suction filter, dry the obtained solid, and recrystallize with ethanol , to 1.55g, yield 90%.

[0041] Dissolve 1.55 g (7.37 mmol) of 2-(2-hydroxyphenyl)benzimidazole in 10 g of concentrated sulfuric acid, heat it in a water bath for 2 h, inject 10 times the amount of water into the reactant, and let it stand for a while A sulfonic acid is then precipitated. First neutralize the sulfonation solution with an appropriate amount of calcium bicarbonate to convert the product into a water-soluble sodium salt, and filter out wat...

Embodiment 2

[0047] Take 1.0 g (8.19 mmol) of salicylaldehyde and 0.94 g (9.00 mmol) of sodium sulfonate, and dissolve them in 25 mL of 95% ethanol to form a solution. At room temperature, it was placed in a 50 mL round bottom flask and reacted for 4 h under magnetic stirring to form a precipitate. Then add 0.97 g (9.0 mmol) o-phenylenediamine and 25 mL DMF to the round bottom flask, heat to reflux for 2 h, pour 10 times the amount of water into the solution, suction filter, dry the obtained solid, and recrystallize with ethanol, 1.53 g was obtained with a yield of 89%.

[0048] Dissolve 1.53 g (7.29 mmol) of 2-(2-hydroxyphenyl)benzimidazole in 10 g of concentrated sulfuric acid, heat it in a water bath for 2 h, inject 10 times the amount of water into the reactant, and let it stand for a while A sulfonic acid precipitated. First neutralize the sulfonation solution with an appropriate amount of calcium bicarbonate to convert the product into a water-soluble sodium salt, and filter out wa...

Embodiment 3

[0050] Take 1.0 g (8.19 mmol) of salicylaldehyde and 1.02 g (9.83 mmol) of sodium sulfonate, and dissolve them in 25 mL of 95% ethanol to form a solution. At room temperature, it was placed in a 50 mL round bottom flask and reacted for 4 h under magnetic stirring to form a precipitate. Then add 1.06 g (9.83 mmol) o-phenylenediamine and 25 mL DMF to the round bottom flask, heat to reflux for 2 h, pour 10 times the amount of water into the solution, suction filter, dry the obtained solid, and recrystallize with ethanol , the yield was 91%.

[0051] Dissolve 1.57 g (7.45 mmol) of 2-(2-hydroxyphenyl)benzimidazole in 10 g of concentrated sulfuric acid, heat it in a water bath for 2 h, inject 10 times the amount of water into the reactant, and let it stand for a while A sulfonic acid precipitated. First neutralize the sulfonation solution with an appropriate amount of calcium bicarbonate to convert the product into a water-soluble sodium salt, and filter out water-insoluble impuri...

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Abstract

The invention discloses a method for improving water solubility of a hydroxybenzimidazolyl compound. The method comprises the following steps: firstly condensing salicylaldehyde with o-phenylenediamine by taking sodium hydrogen sulfite as a condensing agent to prepare 4-hydroxy-3-benzimidazol-2-sulfonic acid (a compound I); then carrying out sulfonation on the compound I by taking concentrated sulfuric acid as a sulfonating agent, and carrying out alkali treatment to prepare 4-hydroxy-3-benzimidazol-2-sodium benzene sulfonate (a compound II). The method has the beneficial effects that the operation is easy, hydroxybenzimidazolyl sulfoacid derivatives are good in water solubility, and the application and development of hydroxybenzimidazol compounds as fluorescent probe molecules are further promoted.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis and relates to a method for improving the water solubility of hydroxybenzimidazole-based compounds. Background technique [0002] Hydroxyphenylbenzimidazoles are an important class of fluorescent compounds, which have strong fluorescence intensity and fluorescence quantum yield, especially large Stokes shifts, and can be used as fluorescent emissive groups for small molecule fluorescent probes. The problem is that the solubility of such fluorescent compounds in water is small, and the application is limited. It is necessary to increase the solubility of such compounds appropriately. [0003] The water solubility and biocompatibility of the probe molecule can be improved by introducing a sulfonic acid group into the molecule through a sulfonation reaction. The sulfo group on the aromatic ring can also be converted into hydroxyl, amino, chloro, cyano, etc., thereby producing a series of...

Claims

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Application Information

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IPC IPC(8): C07D235/18
CPCC07D235/18
Inventor 陈喆张宁杨昕
Owner 天津药物研究院药业有限责任公司
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