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Oxalyl aminoquinoline derivative fluorescent molecular probe and preparation method and application thereof

A fluorescent molecular probe, oxamidoquinoline technology, which is applied in the field of biological fluorescent molecular probes, can solve the problems of many kinds of synthetic raw materials, harsh synthetic conditions, etc., and achieves the advantages of not harsh conditions, simple preparation method and easy-to-obtain raw materials. Effect

Inactive Publication Date: 2016-07-06
QIQIHAR UNIVERSITY
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  • Claims
  • Application Information

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Problems solved by technology

[0003] The present invention aims to solve the technical problems of existing molecular probe synthesis raw materials with many types and harsh synthesis conditions, and provides a class of fluorescent molecular probes of oxamidoquinoline derivatives and their preparation methods and applications, broadening the range of quinolines. Types of fluorescent molecular probes

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  • Oxalyl aminoquinoline derivative fluorescent molecular probe and preparation method and application thereof
  • Oxalyl aminoquinoline derivative fluorescent molecular probe and preparation method and application thereof
  • Oxalyl aminoquinoline derivative fluorescent molecular probe and preparation method and application thereof

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specific Embodiment approach 1

[0026] Specific embodiment one: The general structural formula of the oxalamidoquinoline derivative fluorescent molecular probe of the present embodiment is:

[0027] wherein R is alkoxy, amino, alkylamino, arylamino or hydroxyalkyl.

specific Embodiment approach 2

[0028] Specific embodiment two: the preparation method of the fluorescent molecular probe of oxamidoquinoline derivative described in specific embodiment one is as follows:

[0029] 1. Mix 8-aminoquinoline and diethyl oxalate according to the molar ratio of 1: (5-10), heat up to 150-220°C, and react for 3-12 hours to obtain a reaction mixture. After the reaction mixture is purified, Obtain the intermediate, represented by EOQ;

[0030] 2. Mix EOQ and amine according to the molar ratio of 1: (2~10), heat up to 80~150°C, react for 2~12 hours to obtain crude product I; after purifying the obtained crude product I, obtain monosubstituted oxalyl Aminoquinoline derivative fluorescent molecular probe; the amine is ammonia, organic primary or secondary amine.

specific Embodiment approach 3

[0031] Embodiment 3: The difference between this embodiment and Embodiment 2 is that the molar ratio of 8-aminoquinoline to diethyl oxalate is 1:8. Others are the same as in the second embodiment.

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Abstract

The invention relates to a biological fluorescent molecular probe and its synthetic method and application, in particular to an oxalyl aminoquinoline derivative fluorescent molecular probe and a preparation method and application thereof and aims to solve the technical problem that an existing molecular probe is made from various synthetic materials under harsh synthetic conditions. A structural general formula of the oxalyl aminoquinoline derivative fluorescent molecular probe is shown as follows; wherein R is an alkoxy group, an amino group, an alkyl amino group, an aromatic amino group or a hydroxyl alkyl group. A first preparation method comprises: reacting 8-aminoquinoline with diethyl oxalate to prepare an intermediate, and reacting the intermediate with amine to obtain a mono-substituted oxalyl aminoquinoline derivative fluorescent molecular probe; a second preparation method comprises: adding 8-aminoquinoline and diethyl oxalate into diethyl oxalate for reacting, and purifying to obtain a bis-substituted oxalyl aminoquinoline derivative fluorescent molecular probe. The molecular probe is useful in detecting zinc ions that are zinc ions in a solution or zinc ions in an organism.

Description

technical field [0001] The invention relates to a biological fluorescent molecular probe, its synthesis method and application. Background technique [0002] Aminoquinoline and its derivatives have been made into fluorescent sensors due to their good stability, easy molecular modification, and good biocompatibility, which are widely used in the fields of medicine, dyes, and pesticides to quantitatively detect metal ions. Such as Zhang Yu, Guo Xiangfeng, etc. in "Organic Chemistry Letters" (OrganicLetters) 2008 the 10th issue of the 473-476 article "carboxamido quinoline derivatives with alkoxyethylamine chain as binding group as "Ratiometric and Water-Soluble Fluorescent Zinc of Carboxamidoquinoline with Alkoxyethylamino Chains Receptor" discloses a fluorescent molecular probe of acetamidoquinoline derivatives, which can selectively detect zinc ions. The preparation of fluorescent molecular probes is firstly the reaction of 2-chloroacetyl chloride and 8-aminoquinoline, and ...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D215/40G01N21/64
CPCC07D215/40C09K11/06C09K2211/1022C09K2211/1029G01N21/6428G01N21/643
Inventor 郭祥峰田秀娟于法硕贾丽华
Owner QIQIHAR UNIVERSITY
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