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Chromone oxadiazole compound as well as preparation method and application thereof

A technology of chromone-linked oxadiazole and compound, which is applied in the field of chromone-linked oxadiazole compound and its preparation, can solve the problems of high toxicity and high cost, and achieve the effect of extensive research prospects

Pending Publication Date: 2021-10-29
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the deficiencies of the prior art, the present invention provides a chromone-oxadiazole compound and its preparation method and application, which solves the technical problems of high toxicity and high cost of conventional preparation methods of such compounds

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Pass through figure 1 The steps shown are synthetic intermediate F, i.e. N'-色 ketone-benzoyl hydrazide, and the structural formula is as follows:

[0024] The specific preparation process is: Take 1 mmol of substituted benzoxide hydrazide and 1 mmol 6-substituted-3-formyl ketone mixed in 25 ml of ethanol, add 3 drops of HOAc, and stirred at room temperature for 6 h. There is white turbidity generation, TLC monitors until the reaction is complete, there is a new compound generation. The filtration was filtered, ethanol was washed multiple times until the TLC was removed in the filtrate, and the reactant was reactive. Dry cakes to get pure powder products.

Embodiment 2

[0026] (1) Compound I-1, i.e. Show:

[0027] Preparation process figure 2 As shown, specifically: 0.9865 g (2.74 mmol) N '- ((4-oxo-4H-ketone-3-) methylene) -4- (trifluoromethyl) benzoylide hydrazide and 1.413 G (3.28mmol, 1.2 times) IBD solid mixed in 20 mlch 2 CL 2 The reaction was stirred at room temperature. After about 10 min, the reaction system gradually became clear. After 1 hours, the reaction system was completely yellow, and TLC monitors showed that the reactants were transformed. Steamed removal CH 2 CL 2 20 ml of EtOAc was added, stirred at room temperature for 10 min, filtration, EtOAc.

[0028] The resulting pure product was white powder, the yield was 70%, the melting point was 236-240 ° C, the molecular formula was c 18 Hide 9 Fly 3 N 2 O 3 The result of the test is 1 H NMR (600MHz, CDCL 3 Δ8.87 (S, 1H, = CH-O), 8.42-7.47 (M, 8H, ARH). MS (EI) M / Z: 358.01 (M) + .Anal.calcd for c 18 Hide 9 Fly 3 N 2 O 3 C, 60.34; H, 2.53; N, 7.82.Found: C, 60.52; H, 2.61; N, 7.6...

Embodiment 3

[0069] The 20 compounds of the above synthesis were carried out by CY-FBP / SBPaser inhibitory experiments. CY-FBP / SBPase can catalyze hydrolyzed sugar-1,6-diphosphate as fructose-6-phosphate (F6P) and inorganic phosphate (Pi). The product Pi can form a blue-green complex with a blue-green complex of the alkaline dye peacock green and ambient ammonium molybdate in the presence of polyol, and can be determined by detecting changes in ultraviolet absorbance values ​​at 620 nm at 620 nm. -Fbp / sbpase enzyme activity, thereby detecting the suppression effect of the above compound on CY-FBP / SBPase.

[0070] The specific experiment process is as follows:

[0071] (1) 50 mM Tris-HCl (pH 8.0), 15mm MgCl in the reaction system 2 , 10mm DTT, suitable concentration of CY-FBP / SBPase and a certain concentration gradient inhibitor;

[0072] (2) Add 0.5 mM substrate (FBP) to start the reaction, and incubated at 37 ° C for 5 min, the catalytic reaction was terminated at 1 M Hybridic acid; ...

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Abstract

The invention discloses a chromone bisoxadiazole compound and a preparation method and application thereof. The preparation method comprises the following step of: adding an intermediate F and di (acetoxy) iodobenzene into dichloromethane to carry out a reaction to obtain the chromone bisoxadiazole compound. According to the novel chromone oxadiazole compound and the preparation method thereof, the defects that a traditional method is high in toxicity and high in preparation cost are overcome, and the obtained chromone oxadiazole compound of a novel structure has wide research prospects in new drug research.

Description

Technical field [0001] The present invention relates to the field of chemical synthesis, and in particular, a chromophoreoxazole compound and a preparation method thereof. Background technique [0002] Heterocyclic compounds developed in the past one hundred years play an important role in the treatment of various diseases. Among them, the oxazole compound containing nitrogen-containing atoms and oxygen atoms has many unique properties and biological activity, such as antifungal, anti-tuberculosis, insecticides, herbicide, anti-cancer, anti-inflammatory, antioxidant, etc., also have anti-malarial, anti-anti-anti-anti-malarial Virus, anti-allergic, anti-tumor, analgesic sedation, diuretic, hypnosis. [0003] Drug chemistry is a kind of important pharmacological group, often used in the research and development of new drugs, widely used in drug chemistry research. Therefore, combining the malodorizolic pharmaceutical effect group and the osalone, it is designed and synthesized, and...

Claims

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Application Information

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