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A class of quinoxaline-n containing thiazolidinone structure 1 ,n 4 - Dioxide derivatives, preparation methods and applications thereof

A thiazolidinone and dioxide technology, applied in the field of biochemistry, can solve the problems of poor activity, poor activity of epidermal fungi and deep fungi, poor antibacterial activity of Candida albicans, etc.

Active Publication Date: 2021-03-16
HUAZHONG AGRI UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Studies by Tandon and others have shown that quinoxaline compounds have certain inhibitory effects on Candida albicans and other fungi, and the MIC of individual compounds against Candida albicans and Cryptococcus neoformans is as low as 6.25 μg / mL (Tandon et al., 2006 ); Zhao et al. determined the activity of acemethaquine and quinocetone against a variety of fungi, and the results showed that acemethaquine and quinocetone had poor activity against a variety of epidermis fungi and deep fungi. The MIC is 32 μg / mL, and the MIC of other fungi is greater than 64 μg / mL, and the activity is poor. The MIC of the bacteria was 8 μg / mL (Yan Zhao et al., 2016); Carta et al. determined the antibacterial activity of quinoxaline derivatives against Candida fungi, and the results showed that quinoxaline derivatives were effective against clinically isolated Candida albicans has poor antibacterial activity, with MIC greater than 7.8μg / mL (Carta et al., 2002)

Method used

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  • A class of quinoxaline-n containing thiazolidinone structure <sup>1</sup> ,n <sup>4</sup> - Dioxide derivatives, preparation methods and applications thereof
  • A class of quinoxaline-n containing thiazolidinone structure <sup>1</sup> ,n <sup>4</sup> - Dioxide derivatives, preparation methods and applications thereof
  • A class of quinoxaline-n containing thiazolidinone structure <sup>1</sup> ,n <sup>4</sup> - Dioxide derivatives, preparation methods and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 7-CH3 -2-(3'-phenyl-4'(5H)-thiazolone)-quinoxaline-N 1 ,N 4 -The synthesis reaction formula of dioxide oxide (7) is as follows:

[0036]

[0037] The preparation steps are as follows:

[0038] (1) Add 7.6g (0.05mol) of 4-CH3-2-nitroaniline to a 500mL three-necked flask, add 75mL of anhydrous methanol to dissolve it, add 0.6g (0.015mol) of sodium hydroxide as a catalyst, and 240mL sodium hypochlorite (5%) was added dropwise, and the reaction was stirred for 2 hours. After the reaction was complete, the reaction solution was extracted with dichloromethane, the organic phase was collected and the solvent was removed under reduced pressure to obtain 6.5 g of a light yellow solid, namely 6-CH3-N - Oxybenzofurazan, yield 86.6%.

[0039] (2) Add 15g (0.1mol) 6-CH3-N-benzofurazan oxide, 14.2g (0.12mol) acetone aldehyde dimethyl acetal (Pyruvic aldehyde dimethyl acetal, PDA) and 25mL isopropanol to a 250mL single-necked flask (IPA), stirred to dissolve it, added dropwise ...

Embodiment 2

[0044] 7-CH 3 -2-(3'-(4-CH 3 -phenyl)-4'(5H)-thiazolone)-quinoxaline-N 1 ,N 4 -The synthetic reaction formula of dioxide oxide (8) is as follows:

[0045]

[0046] The preparation steps are as follows:

[0047] (1) Add 7.6g (0.05mol) 4-CH to a 500mL three-necked flask 3 -2-Nitroaniline, add 75mL of anhydrous methanol to dissolve it, add 0.6g (0.015mol) of sodium hydroxide as a catalyst, add 240mL of sodium hypochlorite (5%) dropwise at 0°C, and stir for 2 hours. After the reaction is complete The reaction solution was extracted with dichloromethane, the organic phase was collected and the solvent was removed under reduced pressure to obtain 6.5 g of a light yellow solid, namely 6-CH 3 -N-benzofurazan oxide, yield 86.6%.

[0048] (2) Add 15g (0.1mol) 6-CH to a 250mL single-necked flask 3 -N-benzofurazan oxide, 14.2g (0.12mol) aceguvaldehyde dimethyl acetal and 25mL isopropanol, stirred and dissolved, added dropwise 2mL tetrahydropyrrole (99%), stirred and reacted at 2...

Embodiment 3

[0053] 7-F-2-(3'-phenyl-4'(5H)-thiazolone)-quinoxaline-N 1 ,N 4 -The synthetic reaction formula of dioxide oxide (17) is as follows:

[0054]

[0055] The preparation steps are as follows:

[0056] (1) Add 7.8g (0.05mol) of 4-F-2-nitroaniline to a 500mL three-necked flask, add 75mL of anhydrous methanol to dissolve it, add 0.6g (0.015mol) of sodium hydroxide as a catalyst, and 240mL sodium hypochlorite (5%) was added dropwise, and the reaction was stirred for 2 hours. After the reaction was complete, the reaction solution was extracted with dichloromethane, the organic phase was collected and the solvent was removed under reduced pressure to obtain 6.5 g of a light yellow solid, which was 6-F-N-oxidation Benzofurazan, yield 83.3%.

[0057] (2) Add 15.4g (0.1mol) 6-F-N-benzofurazan oxide, 12mL (0.2mol) acetone and 50mL triethylamine to a 100mL single-necked flask, stir to dissolve, add dropwise 0.5mL tetrahydropyrrole (99% ), after stirring and reacting at room temperatu...

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Abstract

The invention belongs to the technical field of biochemistry, and particularly relates to a quinoxaline-N1, N4-dioxide derivative containing a thiazolidinone structure as well as a preparation methodand application thereof. The thiazolidinone structure is combined with quinoxaline-N1, N4-dioxide, a novel quinoxaline-N1, N4-dioxide derivative is designed and synthesized, and the novel quinoxaline-N1, N4-dioxide derivative has a certain inhibitory activity on candida. In the plurality of compounds prepared by the method in the invention, the antibacterial activity of 12 compounds on candida isless than or equal to 8 mug / mL, the compound 20, namely 7-F-2-(3'-(4-F-phenyl)-4'(5H)-thiazolone)-quinoxaline-N1, N4-dioxide, has the best activity, and the MIC to candida tropicalis (ATCC7349) and candida parapsilosis (ATCC22019) is 2 mug / mL.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, in particular to a class of quinoxaline-N containing thiazolidinone structure 1 ,N 4 - Dioxide derivatives, methods of preparation and applications thereof. Background technique [0002] Quinoxaline-N 1 ,N 4 -Quinoxalines-1,4-dioxide is a kind of chemically synthesized benzopyrazine heterocyclic compound, which has good antibacterial activity and can improve feed conversion rate, and is widely used in veterinary clinics (Novacek et al. al., 1982; Cihak et al., 1985). In recent years, studies have found that quinoxaline drugs also have anti-tumor (Rajkumar et al., 2012; Tania et al., 2012), anti-tuberculosis (Andrés et al., 2005), anti-viral (Vijay et al., 2011 ), antiparasitic (Dinorah et al., 2011), antifungal (Yan Zhao et al., 2016), anaerobic selective cytotoxicity (Gali-Muhtasib et al., 2001), etc. Studies by Tandon and others have shown that quinoxaline compounds have certain inhi...

Claims

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Application Information

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IPC IPC(8): C07D417/04A61K31/498A61P31/10A23K20/137
CPCA23K20/137A61P31/10C07D417/04
Inventor 袁宗辉张鹤营潘源虎张洁黄玲利瞿玮谢书宇陈冬梅陶燕飞王玉莲王旭刘振利
Owner HUAZHONG AGRI UNIV