Quinolone imidazole compound as well as preparation method and application thereof

A technology of quinolone imidazoles and compounds, which is applied in the field of quinolone imidazoles and their preparations, can solve the problems that traditional medicines cannot exert high-efficiency effects, and achieve the effects of solving drug resistance, short synthesis route, and simple preparation of raw materials

Active Publication Date: 2019-03-29
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the frequent occurrence of bacterial resistance makes traditional drugs unable to play an efficient role. Most bacteria have developed resistance to commonly used antibiotics, especially in developing countries. Therefore, the development of antibacterial drugs with new structures It has become very urgent, especially the research and development of some antibacterial drugs with high efficiency, low toxicity and low drug resistance has attracted widespread attention

Method used

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  • Quinolone imidazole compound as well as preparation method and application thereof
  • Quinolone imidazole compound as well as preparation method and application thereof
  • Quinolone imidazole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of Intermediates V-VII

[0042]

[0043] Reference "Cui Sheng-Feng, Addla Dinesh, Zhou Cheng-He. Novel 3-Aminothiazolquinolones: Design, Synthesis, Bioactive Evaluation, SARs, and Preliminary Antibacterial Mechanism. Journal of Medicinal Chemistry, 2016, 59, 4488-4510" disclosed method for preparation. Obtained 2.45g of intermediate V with a yield of 70.1%, black oily liquid; obtained 2.59g of intermediate VI with a yield of 76.3% as a brown solid; obtained 3.05g of intermediate VII with a yield of 52.8% as a brown solid.

Embodiment 2

[0045] Preparation of Intermediate VIII

[0046]

[0047] In a 250mL round bottom flask, add intermediate VII (1g, 4.48mmol) and potassium carbonate (1.86g, 13.45mmol) in 25mL of N,N-dimethylformamide at 100°C for 1h, then add bromoethanol (0.35 mL, 4.93mmol), stirred at 100°C for 24h. Thin-layer chromatography tracked to the end of the reaction, cooled to room temperature (18-25°C), and then concentrated, filtered, column chromatographically separated, dried and other post-treatments to obtain 1.10g of compound VIII, with a yield of 10.84% ​​and a melting point of 242°C , brown solid. 1 H NMR (600MHz, DMSO-d 6 )δ8.53 (s, quinolone-5-H, 1H), 7.51–7.44 (m, quinolone-10-H, 1H), 7.32–7.26 (m, quinolone-8-H, 1H), 4.54 (d, J=4.2Hz, C2-OCH 2 ,2H),4.45(d,J=4.0Hz,C3-NCH 2 ,2H),2.61(s,-CH 3 ,3H).

Embodiment 3

[0049]Preparation of Intermediate IX:

[0050]

[0051] Intermediate VIII (0.40 g, 1.62 mmol) was stirred in acetic acid (10 mL) at 0 °C, bromine (0.13 g, 2.43 mmol) was added to the reaction mixture, and then stirred at 60 °C for 12 h. After the reaction was complete, the reaction mixture was cooled to room temperature, diluted with 25 mL of water, and the resulting solid was filtered and washed twice with water to remove acetic acid. After concentration, separation by column chromatography, drying and other post-treatments, intermediate IX was obtained with a yield of 28.6%, a melting point of 240° C., and a brown solid. 1 H NMR (600MHz, DMSO-d 6 )δ8.67(s,1H,quinolone-5-H),7.50(dd,J=9.1,2.0Hz,1H,quinolone-10-H),7.33(dd,J=9.4,2.2Hz,1H,quinolone -8-H),4.91(s,2H,CH 2 Br), 4.58–4.55 (m, 2H, OCH 2 ),4.52–4.46(m,2H,NCH 2 ).

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Abstract

The invention relates to a quinolone imidazole compound as well as a preparation method and application thereof, and belongs to the technical field of chemical synthesis. The quinolone imidazole compound is shown as general formulas I-IV. The compound has certain inhibition activity on one or several kinds of materials in gram positive bacteria, gram-negative bacteria and fungi, and can be used for preparing anti-bacterial and/or anti-fungal medicine, so that the compound has the opportunity to provide more safe efficient and diversified alternative medicine for clinic antimicrobial treatment;the clinic treatment problems of daily serious drug resistance, stubborn pathogenic microbes, newly occurring harmful microbes and the like can be favorably solved. The preparation raw materials aresimple; the price is low; the obtaining is easy; the synthesis path is short; important significance is realized in aspect of infection resistance. The formulas are shown in the description.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to quinolone-imidazole compounds and their preparation methods and applications. Background technique [0002] Microbial infection has been a major problem threatening human health for many years. There are many types of antibacterial drugs on the market, including natural antibiotics and chemically synthesized antibacterial drugs, so there are more room for clinical selection, such as cephalosporins and penicillins are anti-infective drugs that are widely used clinically and in large quantities. However, the frequent occurrence of bacterial resistance makes traditional drugs unable to play an efficient role. Most bacteria have developed resistance to commonly used antibiotics, especially in developing countries. Therefore, the development of antibacterial drugs with new structures It has become very urgent, especially the research and development of some ant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/06A61P31/04A61P31/10A61K31/5383
CPCA61P31/04A61P31/10C07D498/06Y02A50/30
Inventor 周成合巴绨倪·纳塞亚李珍珍
Owner SOUTHWEST UNIVERSITY
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