Quinoline derivative as well as preparation method and application thereof

A derivative, quinoline technology, applied in the field of quinoline derivatives and their preparation, can solve the problems of limitations, lack of universality, quinoline derivative fluorescein cannot be used to label small molecular compounds, etc., and meet the reaction conditions Mild, broadened selection range, and stable fluorescence properties

CN112824392AInactive Publication Date: 2021-05-21CHINA AGRI UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2021-05-21
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention relates to the technical field of chemical engineering, and particularly discloses a quinoline derivative as well as a preparation method and application thereof. The quinoline derivative has the following structure: the surface of the quinoline derivative has a high-activity carboxyl group which can be directly used for marking, and the quinoline derivative has a blue emission wavelength, so that the blank of the conventional organic dye fluorescein in a low wavelength band at present is filled, and the fluorescein selection range of multiple marking modes is widened. In addition, the quinoline derivative has good light stability, is stable in an organic reagent, can maintain good fluorescence characteristics, and is suitable for labeling reaction in an organic solvent. The preparation method of the quinoline derivative comprises the following steps: carrying out amidation, oximation and reduction reaction on 4-benzoylbutyric acid, firstly synthesizing a side chain of the quinoline derivative, and then carrying out condensation reaction on the side chain and 6-bromoquinoline to synthesize the final quinoline derivative. The method is simple and mild.
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Description

technical field

[0001] The invention relates to the technical field of chemical industry, in particular to a quinoline derivative and its preparation method and application. Background technique

[0002] The parent structure of quinoline derivatives is quinoline, which was first isolated from coal tar. Quinoline derivatives are a very important class of heterocyclic compounds. Due to their obvious pharmacological and biological activities, they have been widely used in the fields of drug screening, dye industry and chemical analysis. A large number of studies have shown that many compounds with quinoline rings have obvious biological and pharmacological activities such as antibacterial, bactericidal, analgesic, antiallergic, antimalarial, antitumor, anticancer, antihypertensive, antidepressant and memory enhancement, and In recent years, quinoline derivatives have also been used to develop drugs for the treatment of AIDS. In addition, due to the excellent optical propertie...

Examples

Embodiment 1

[0072] This embodiment provides a quinoline derivative of the present invention and a preparation method thereof.

[0073] Concrete preparation steps are as follows:

[0074] (1) 4-benzoyl butyric acid is subjected to amidation reaction to obtain compound I:

[0075] Dissolve 119g (100mmol) of 4-benzoylbutyric acid in 500mL of dichloromethane (DCM), then add 8.97g (110mmol) of dimethylamine hydrochloride, 50mL of N,N-diisopropylethylamine (DIPEA ), 41.80g (110mmol) tetramethylurea hexafluorophosphate (HATU), stirred at room temperature 25°C for 16h, after the reaction, washed with 500mL water each time, repeated twice, then dried with anhydrous sodium sulfate, centrifuged The precipitated substance was taken and separated by thin-layer chromatography (the developing solvent was dichloromethane / methanol (v / v, 50:1)) to obtain 14.25 g of compound I with a yield of 65%.

[0076] (2) subjecting the compound I to an oximation reaction to obtain compound II;

[0077] 14.25g (65mm...