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A r-2-substituted-3-nitro-2h-chromene derivative with antibacterial activity and its preparation method and application

A technology of R-2-, antibacterial activity, applied in organic chemical methods, antibacterial drugs, organic chemistry, etc., can solve problems such as low recovery rate

Active Publication Date: 2020-07-07
SOUTHWEST UNIV
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  • Application Information

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Problems solved by technology

However, the above-mentioned methods always have some unavoidable defects, such as moderate enantioselectivity, low recovery or special substrates that require modification, so the development of organic small molecule-catalyzed 3-nitro-2H-chromene derivatives A new method of asymmetric synthesis and its antibacterial activity are of great significance in the treatment of bacterial infectious diseases

Method used

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  • A r-2-substituted-3-nitro-2h-chromene derivative with antibacterial activity and its preparation method and application
  • A r-2-substituted-3-nitro-2h-chromene derivative with antibacterial activity and its preparation method and application
  • A r-2-substituted-3-nitro-2h-chromene derivative with antibacterial activity and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: Preparation of (R)-2-(3-nitro-2H-chromene) ethyl acetate I-1:

[0024] At room temperature, add 3-(2-formylphenoxy)ethyl acrylate II-1 (0.2mmol, 1.0equiv), nitromethane (1mmol, 5equiv) and catalyst (0.01mmol, 0.1equiv) to the sealed tube ) and PhCF 3 (0.5 mL). The reaction mixture was stirred at room temperature for 72 h, and the reaction was detected by TLC. After the reaction, the crude product was purified by silica gel column chromatography and eluted with petroleum ether / ethyl acetate (20:1) to obtain 15.0 mg of yellow oily liquid with a yield of 27%. Using petroleum ether / ethyl acetate=10 / 1 mixed solution as developing solvent, R f =0.23, the preparation obtains (R)-2-(3-nitro-2H-chromene) ethyl acetate I-1, and its chemical structural formula is as follows:

[0025]

[0026] 1 H NMR (400MHz, CDCl 3 ): δ (ppm) = 7.85 (s, 1H), 7.38 (td, J = 8.2, 1.6Hz, 1H), 7.29 (dd, J = 7.6, 1.6Hz, 1H), 7.04 (td, J = 7.5, 1.1Hz, 1H), 6.94(d, J=8.2Hz, 1H), 6...

Embodiment 2

[0031] Embodiment 2: Preparation of (R)-2-(6-methoxy-3-nitro-2H-chromene) ethyl acetate I-2

[0032]Add ethyl 3-(2-formyl-4-methoxyphenoxy)acrylate II-2 (0.2 mmol, 1.0 equiv), nitromethane (1 mmol, 5 equiv) and catalyst to the sealed tube at room temperature (0.01mmol, 0.1equiv) and PhCF 3 (0.5 mL). The reaction mixture was stirred at room temperature for 72 h, and the reaction was detected by TLC. After the reaction, the crude product was purified by silica gel column chromatography and eluted with petroleum ether / ethyl acetate (20:1) to obtain 31.5 mg of yellow oily liquid with a yield of 27%. Use petroleum ether / ethyl acetate=10 / 1 mixed solution as developing solvent, R f =0.3, compound I-2 is prepared, and its chemical structural formula is as follows:

[0033]

[0034] 1 H NMR (400MHz, CDCl 3 ):δ(ppm)=7.80(s,1H),6.95(dd,J=8.9,2.9Hz,1H),6.89-6.84 (m,1H),6.79(d,J=2.9Hz,1H),5.98 (dd,J=9.5,3.6Hz,1H),4.23-4.13(m,2H),3.79(s,3H), 2.83(dd,J=15.0,9.5Hz,1H),2.66(dd,J=15.0...

Embodiment 3

[0039] Embodiment 3: Preparation of (R)-2-(7-methoxy-3-nitro-2H-chromene) ethyl acetate I-3

[0040] Add ethyl 3-(2-formyl-5-methoxyphenoxy)acrylate II-3 (0.2 mmol, 1.0 equiv), nitromethane (1 mmol, 5 equiv) and catalyst to the sealed tube at room temperature (0.01mmol, 0.1equiv) and PhCF 3 (0.5 mL). The reaction mixture was stirred at room temperature for 72 h, and the reaction was detected by TLC. After the reaction, the crude product was purified by silica gel column chromatography and eluted with petroleum ether / ethyl acetate (20:1) to obtain 14.3 mg of yellow oily liquid with a yield of 12%. Use petroleum ether / ethyl acetate=10 / 1 mixed solution as developing solvent, R f =0.25, compound I-3 is prepared, and its chemical structural formula is as follows:

[0041]

[0042] 1 H NMR (400MHz, CDCl 3 ): δ (ppm) = 7.85 (s, 1H), 7.20 (d, J = 8.5Hz, 1H), 6.60 (dd, J = 8.5, 2.4Hz, 1H), 6.47 (d, J = 2.4Hz, 1H ),6.04(dd,J=9.5,3.4Hz,1H),4.20(dtq,J=10.8,6.8,3.7Hz,2H),3.83(s,3...

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Abstract

The invention discloses an R-2-substituted-3-nitro-2H-chromene derivative with antibacterial activity and a preparation method and application thereof. The R-2-substituted-3-nitro-2H-chromene derivative belongs to chiral compounds of R configuration. The preparation method is easy. The R-2-substituted-3-nitro-2H-chromene derivative is prepared through organic catalysis of a salicylaldehyde derivative and nitromethane in a 'one-pot method'. Compared with a raceme, the effective single configuration of product obtained through asymmetrical synthesis has higher antibacterial activity, eliminatingimpact of another ineffective configuration. The R-2-substituted-3-nitro-2H-chromene derivative is represented by using the means of 1H NMR, 13C NMR, HRMS, a polarimeter and the like. Optical pure R-2-substituted-3-nitro-2H-chromene derivative has high antibacterial activity, and can be used for preparing chiral antibacterial agents.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to an R-2-substituted-3-nitro-2H-chromene derivative with antibacterial activity and a preparation method and application thereof. Background technique [0002] Antibiotics are currently the most widely used antibacterial drugs. However, with the widespread use and abuse of antibiotics, various multidrug-resistant strains and superbugs appear, posing potential threats to human health and survival. Therefore, the research and development of new antibacterial drugs with good antibacterial activity and not easy to produce drug resistance is not only imminent, but also has important scientific research significance, which will help to solve the crisis of bacterial drug resistance. [0003] 2H-chromene is an important component of many natural products, drug molecules and biologically active substances. 2H-chromenes have been reported to have significant antibacterial, antioxi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/04C07D311/58C07D311/92A61P31/04
CPCA61P31/04C07B2200/07C07D311/04C07D311/58C07D311/92
Inventor 任巧袁吕江李木瑶赵筱斐杨文
Owner SOUTHWEST UNIV
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