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R-2-substituted-3-nitro-2H-chromene derivative with antibacterial activity and preparation method and application thereof

An R-2-, antibacterial activity technology, applied in organic chemical methods, antibacterial drugs, organic chemistry and other directions, can solve problems such as low recovery rate, achieve good bactericidal performance, good application value, and reduce the effect of dosage

Active Publication Date: 2018-08-17
SOUTHWEST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • R-2-substituted-3-nitro-2H-chromene derivative with antibacterial activity and preparation method and application thereof
  • R-2-substituted-3-nitro-2H-chromene derivative with antibacterial activity and preparation method and application thereof
  • R-2-substituted-3-nitro-2H-chromene derivative with antibacterial activity and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 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 (0.5mL). The reaction mixture was stirred at room temperature for 72 hours, and the reaction was checked 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%. Use a mixed solution of petroleum ether / ethyl acetate = 10 / 1 as a developing agent, R f =0.23, (R)-2-(3-nitro-2H-chromene) ethyl acetate I-1 was prepared, and its chemical structure is as follows:

[0025]

[0026] 1 H NMR(400MHz, CDCl 3 ): δ (ppm) = 7.85 (s, 1H), 7.38 (td, J = 8.2, 1.6 Hz, 1H), 7.29 (dd, J = 7.6, 1.6 Hz, 1H), 7.04 (td, J = 7.5, 1.1Hz, 1H), 6.94 (d, J = 8.2 Hz, 1H), 6.04 (dd, J = 9.4, 3.6...

Embodiment 2

[0031] Example 2: Preparation of (R)-2-(6-methoxy-3-nitro-2H-chromene) ethyl acetate 1-2

[0032] At room temperature, add 3-(2-formyl-4-methoxyphenoxy) ethyl acrylate II-2 (0.2mmol, 1.0 equiv), nitromethane (1mmol, 5equiv) and catalyst to the sealed tube (0.01mmol, 0.1equiv) and PhCF 3 (0.5mL). The reaction mixture was stirred at room temperature for 72 hours, and the reaction was checked 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 a mixed solution of petroleum ether / ethyl acetate = 10 / 1 as a developing agent, R f = 0.3, compound I-2 is prepared, and its chemical structure 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 , 3.6 Hz,...

Embodiment 3

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

[0040] At room temperature, add 3-(2-formyl-5-methoxyphenoxy) ethyl acrylate II-3 (0.2mmol, 1.0 equiv), nitromethane (1mmol, 5equiv) and catalyst to the sealed tube (0.01mmol, 0.1equiv) and PhCF 3 (0.5mL). The reaction mixture was stirred at room temperature for 72 hours, and the reaction was checked 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 a mixed solution of petroleum ether / ethyl acetate = 10 / 1 as a developing agent, R f =0.25, compound I-3 is prepared, and its chemical structure is as follows:

[0041]

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

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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 particularly 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 application of antibiotics and their abuse, leading to the emergence of various multi-drug resistant strains and super bacteria, there is a potential threat to human health and survival. Therefore, the research and development of new antibacterial drugs with good antibacterial activity and not easy to develop drug resistance is not only imminent, but also has important scientific research significance and helps solve the crisis of bacterial resistance. [0003] 2H-chromene is an important part of many natural products, drug molecules and biologically active substances. It is reported that 2H-chromene has significant antibacte...

Claims

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Application Information

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Patent Type & Authority Applications(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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