Chromone oxadiazoline compound as well as preparation method and application thereof

A chromone-bioxadiazoline and bioxadiazoline technology, which is applied in the field of chromone-bioxadiazoline compounds and their preparation, can solve the problems of high cost, high toxicity, difficulty in large-scale production and the like, and achieves overcoming Effects of high toxicity and broad research prospects

Active Publication Date: 2021-09-21
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the conventional preparation methods of such compounds are highly toxic and costly, and are not easy to carry out large-scale production. Therefore, proposing a new preparation method is very beneficial to industrial production

Method used

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  • Chromone oxadiazoline compound as well as preparation method and application thereof
  • Chromone oxadiazoline compound as well as preparation method and application thereof
  • Chromone oxadiazoline compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Compound I-1, namely 3-(3-acetyl-5-(4-nitrophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-)-4 -Oxo-4H-chromone-6-carboxylic acid, whose structural formula is as follows:

[0027]

[0028] The specific preparation process is as follows: take 381mg (1mmol) of compound II-1, add 10g (excessive) acetic anhydride, heat and reflux for more than 1h, the reaction solution changes from turbid to clear liquid; TLC monitors the reaction process until the reaction is complete; cooling, add 50mL water, stirring continuously, to completely hydrolyze acetic anhydride, a solid precipitated out, suction filtered, washed with water, dried, and separated by PE / EtOAc column chromatography to obtain the target product.

[0029] The obtained pure product is 127mg of yellow powder, the yield is 30%, the melting point is 227-231°C, and the molecular formula is C 20 h 13 N 3 o 8 , to detect it, and the detection result is: 1 H NMR (600MHz, DMSO-d 6 )δ13.62–13.24(m,1H,COOH),8.95–7.71(m,8H,=...

Embodiment 2

[0085] Cy-FBP / SBPase enzyme inhibition experiments were carried out on the 19 compounds synthesized above. Cy-FBP / SBPase can catalyze the hydrolysis of fructose-1,6-bisphosphate into fructose-6-phosphate (F6P) and inorganic phosphate (Pi). The product Pi can form a blue-green complex with the basic dye malachite green and ammonium molybdate mixture in the presence of polyhexenol, and Cy can be determined by detecting the change in the ultraviolet absorbance value of the complex at 620nM. - Enzyme activity of FBP / SBPase, and then detect the inhibitory effect of the above compounds on Cy-FBP / SBPase.

[0086] The specific experimental process is as follows:

[0087] 1. Add 50mM Tris-HCl (pH 8.0), 15mM MgCl to the reaction system 2 , 10mM DTT, an appropriate concentration of Cy-FBP / SBPase and a certain concentration gradient of the above compounds;

[0088] 2. Add 0.5mM substrate (FBP) to start the reaction, and after incubating at 37°C for 5min, stop the catalytic reaction wit...

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Abstract

The invention discloses a chromone oxadiazoline compound and a preparation method and application thereof. The preparation method comprises the following steps: under the action of acetic anhydride, subjecting a compound shown in a formula II to shrinkage cyclization to obtain an oxadiazoline ring, and subjecting N on the oxadiazoline ring to acetylation reaction under the action of acetic anhydride to obtain a chromone oxadiazoline compound. The invention provides the novel preparation method of the chromone oxadiazoline compound, the defects of high toxicity and high preparation cost of traditional methods are overcome, and the obtained chromone oxadiazoline compound with a novel structure has a wide research prospect in new drug research.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a chromone-oxadiazoline compound and a preparation method and application thereof. Background technique [0002] Chromone compounds have rich biological activities, such as sterilization, anti-inflammation, anti-allergy, etc., and have always been one of the hot research areas of medicinal chemists. Oxadiazolines are an important class of five-membered heterocyclic compounds with good biological activities, such as insecticide, anti-inflammatory, anti-AIDS and promotion of plant growth, so they are favored by medicinal chemists. Therefore, combining chromones and oxadiazolines to design and synthesize excellent ketooxadiazoline series compounds has broad research prospects in new drug research. However, the conventional preparation methods of such compounds are highly toxic and costly, making it difficult to carry out large-scale production. Therefore, pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04A01N43/824A01P13/00
CPCC07D413/04A01N43/82
Inventor 宋伏冰张海雯张怀艺叶惠丹涂其冬熊丹涂艳平汪秀娇谭诗雨缪祖君
Owner JIANGXI SCI & TECH NORMAL UNIV
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