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Hypoboric acid derivative based on 2-(4-dyhydroxy borane)pheoylquinoline-4-carboxylic acid and preparation method and application thereof

A technology of dihydroxyborane and phenylquinoline, which is applied in the field of fluorescence recognition, can solve the problems of high price, unfavorable derivatization and carrying out subject research

Inactive Publication Date: 2017-06-20
INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The raw material is expensive, which is not conducive to the laboratory's systematic derivatization and research

Method used

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  • Hypoboric acid derivative based on 2-(4-dyhydroxy borane)pheoylquinoline-4-carboxylic acid and preparation method and application thereof
  • Hypoboric acid derivative based on 2-(4-dyhydroxy borane)pheoylquinoline-4-carboxylic acid and preparation method and application thereof
  • Hypoboric acid derivative based on 2-(4-dyhydroxy borane)pheoylquinoline-4-carboxylic acid and preparation method and application thereof

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preparation example Construction

[0066] The present invention also includes a method for preparing diboronic acid derivatives based on 2-(4-dihydroxyborane) phenylquinoline-4-carboxylic acid, comprising the following steps:

[0067] ① Dissolve p-bromoacetophenone and isatin in ethanol, add potassium hydroxide solution to it, stir and reflux for 5-10 hours, distill off the ethanol under reduced pressure, adjust the pH to 2-4 with hydrochloric acid, and precipitate a reddish-brown precipitate , to obtain a filter cake by filtration; the filter cake was washed with water and ethyl acetate successively during filtration, and then the filter cake was recrystallized with a mixture of methanol and glacial acetic acid with a volume ratio of 1:1 to obtain 2-(4-bromophenyl)quinoline -4-carboxylic acid;

[0068] Wherein the molar volume ratio of p-bromoacetophenone, isatin, ethanol and potassium hydroxide solution is 1~1.5mol: 1mol: 1~1.5L: 0.5~1L; the concentration of described potassium hydroxide solution is 30~50 %;...

Embodiment 1

[0119] A diboronic acid derivative based on 2-(4-dihydroxyborane)phenylquinoline-4-carboxylic acid with the structure I 1 Shown:

[0120]

[0121] The preparation method of this compound comprises the following steps:

[0122] ①Dissolve 199g of p-bromoacetophenone and 147g of isatin in 1L of ethanol, add 500ml of potassium hydroxide solution with a concentration of 30%, stir and reflux for 5 hours, remove the ethanol by distillation under reduced pressure, and adjust the pH to 2 with hydrochloric acid , precipitated a reddish-brown precipitate, and filtered to obtain a filter cake; when filtering, the filter cake was washed with 500ml of water and 500ml of ethyl acetate in sequence, and then the filter cake was recrystallized with 500ml of methanol and glacial acetic acid mixture with a volume ratio of 1:1 to obtain 2- (4-bromophenyl)quinoline-4-carboxylic acid;

[0123] ② Take 196g of 2-(4-bromophenyl)quinoline-4-carboxylic acid obtained in step ① into the reaction vesse...

Embodiment 2

[0134] A diboronic acid derivative based on 2-(4-dihydroxyborane)phenylquinoline-4-carboxylic acid with the structure I 2 Shown:

[0135]

[0136] The preparation method of this compound comprises the following steps:

[0137] ①Dissolve 298.5g of p-bromoacetophenone and 147g of isatin in 1500ml of ethanol, add 1L of 50% potassium hydroxide solution to it, stir and reflux for 10 hours, remove the ethanol by distillation under reduced pressure, and adjust the pH to 4. Precipitate a reddish-brown precipitate, filter to obtain a filter cake; when filtering, the filter cake is washed with 1000ml of water and 1000ml of ethyl acetate in sequence, and then the filter cake is recrystallized with a mixture of methanol and glacial acetic acid with a volume ratio of 1:1 to obtain 2- (4-bromophenyl)quinoline-4-carboxylic acid;

[0138] ② Take 228.9g of the 2-(4-bromophenyl)quinoline-4-carboxylic acid obtained in step ① into the reaction vessel, add 0.7L of thionyl chloride and a drop ...

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Abstract

The invention discloses a hypoboric acid derivative based on 2-(4-dyhydroxy borane)pheoylquinoline-4-carboxylic acid and a preparation method thereof. The hypoboric acid derivative is used for preparing catecholamine and carbohydrate fluorescent probes. The preparation method comprises the following steps of on one hand, using parabromoacetophenone, isatin and a common reagent as initiating raw materials, and performing Pfitzinger reaction, carboxyl esterification, palladium catalyzing, hydrolyzing and the like, so as to synthesize 2-(4-dyhydroxy borane)pheoylquinoline-4-carboxylic acid (PBAQA); on the other hand, using a diamine compound, singly protecting by di-tert-butyl dicarbonate, performing amide condensation and hydrochloric acid protecting group removal with the PBAQA, and then performing amide condensation with a boronobenzoic acid derivative, so as to obtain the hypoboric acid derivative. The preparation method has the advantages that the prices of raw materials are low, and the obtaining is easy; the yield rate of whole reaction route is higher, the reaction condition is mild, the operation is simple, the requirement on a reaction device is low, the production cost is low, and the hypoboric acid derivative is suitable for large-batch production.

Description

technical field [0001] The invention relates to the technical field of fluorescent recognition for catecholamines and sugar compounds, in particular to a diboronic acid derivative based on 2-(4-dihydroxyborane)phenylquinoline-4-carboxylic acid and a preparation method thereof and uses. Background technique [0002] Catechol structures are widely found in many substances in nature, such as urushiol, gossypol catechin, and hormone neurotransmitters. Many of these compounds are involved in physiological and pathological processes, including inhibiting the release of prolactin from the anterior pituitary gland; acting on the sympathetic nervous system; increasing heart rate and blood pressure; and being used in the treatment of Parkinson's syndrome and Alzheimer's disease, etc. In addition, considering their antimicrobial, antioxidant and anti-inflammatory activities, scientists have invested a lot of effort trying to establish a sensitive, fast and easy method for the detectio...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCY02P20/55C07F5/025C09K11/06C09K2211/1029G01N21/6428
Inventor 吴忠玉孙捷王凯姚庆强孙敬勇刘爱芹
Owner INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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