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Quinolones and benzimidazoles and their preparation methods and applications

A technology of benzimidazoles and compounds, which is applied in the application field of quinolone benzimidazoles and pharmaceuticals, can solve the problems of serious bacterial drug resistance, and achieve the effects of solving drug resistance, simple preparation method and low cost

Active Publication Date: 2018-01-05
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the widespread and inappropriate use of quinolone antibacterial drugs, quinolone-resistant strains continue to emerge, the problem of bacterial resistance is becoming more and more serious, and anti-infection treatment is facing severe challenges

Method used

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  • Quinolones and benzimidazoles and their preparation methods and applications
  • Quinolones and benzimidazoles and their preparation methods and applications
  • Quinolones and benzimidazoles and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1, the preparation of compound I-1

[0042]

[0043] In a 100mL round-bottomed flask, norfloxacin hydrochloride (1.00g, 0.0031mol), potassium carbonate (0.433g, 0.0031mol), potassium iodide (0.515g, 0.0031mol) and appropriate amount of acetonitrile were stirred at 50°C for reaction 0.5h, cooled to room temperature (18~25°C), added chloromethyl benzimidazole (0.516g, 0.0031mol) and controlled the temperature to 45°C to continue stirring, tracked by thin-layer chromatography until the reaction was completed, then concentrated, extracted, column Chromatographic separation and drying gave 0.94 g of compound I-1, with a yield of 67.4%.

[0044] Compound I-1: white powder; melting point 157-158°C; 1 H NMR (600MHz, DMSO-d 6): δ15.34 (s, 1H, COOH), 12.35 (s, 1H, benzimidazole-NH), 8.94 (s, 1H, quinolone 2-H), 7.90 (d, J=13.3Hz, 1H, quinolone 5- H), 7.50 (s, 2H, benzimidazole 4,7-H), 7.17 (s, 1H, quinolone 8-H), 7.16―7.12 (m, 2H, benzimidazole 5,6-H), 4.58 (q, J...

Embodiment 2

[0045] Embodiment 2, the preparation of compound 1-2

[0046]

[0047] In a 100mL round-bottomed flask, ciprofloxacin hydrochloride (1.00g, 0.002mol), potassium carbonate (0.299g, 0.002mol), potassium iodide (0.332g, 0.002mol) and an appropriate amount of acetonitrile were stirred at a temperature of 50°C. 0.5h, cooled to room temperature (18~25°C), added chloromethylbenzimidazole (0.333g, 0.002mol) and controlled the temperature to 45°C to continue stirring, tracked by thin-layer chromatography until the end of the reaction, then concentrated, extracted, column After chromatographic separation and drying, 0.50 g of compound I-2 was obtained, with a yield of 54.0%.

[0048] Compound I-2: yellow powder; melting point 158-159°C; 1 H NMR (600MHz, DMSO-d 6 )δ: 15.20 (s, 1H, COOH), 8.66 (s, 1H, quinolone 2-H), 7.90 (d, J=13.2Hz, 1H, quinolone 5-H), 7.58―7.50 (m, 3H, benzimidazole 4,7-H,quinolone 8-H),7.17(s,2H,benzimidazole 5,6-H),3.88(s,2H,quinolone N-CH 2 ),3.81(s,1H,cyclo...

Embodiment 3

[0049] Embodiment 3, the preparation of compound 1-3

[0050]

[0051] In a 100mL round-bottomed flask, norfloxacin hydrochloride (1.00g, 0.0031mol), potassium carbonate (0.433g, 0.0031mol), potassium iodide (0.515g, 0.0031mol) and appropriate amount of acetonitrile were stirred at 50°C for reaction After 0.5h, cool to room temperature (18~25°C), add the corresponding N-ethylchloromethylbenzimidazole (0.558g, 0.0031mol) and control the temperature to 45°C to continue stirring, track the reaction by thin-layer chromatography until the end of the reaction, and then Concentration, extraction, separation by column chromatography, and drying yielded 0.98 g of compound I-3, with a yield of 66.3%.

[0052] Compound I-3: yellow powder; melting point 151-152°C; 1 H NMR (600MHz, DMSO-d 6 )δ: 15.37 (s, 1H, COOH), 8.98 (s, 1H, quinolone 2-H), 7.94 (d, J=13.1Hz, 1H, quinolone 5-H), 7.63 (dd, J=24.8, 7.9 Hz, 2H, benzimidazole 4,7-H), 7.25 (ddd, J=20.1, 13.5, 7.1Hz, 3H, quinolone8-H, b...

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Abstract

The invention discloses a quinolone benzimidazole compound as well as a preparation method and application thereof. A structure of the compound is shown in a general formula (I) shown in the specification. The compound has antimicrobial activity, has certain inhibitory activities toward gram-positive bacteria, gram-negative bacteria and fungi, is used for preparing antibacterial and / or antifungal medicines and can be combined with pharmaceutical auxiliary materials to prepare single or compound preparations. The compound disclosed by the invention has the beneficial effects that raw materials for preparing the compound have high degrees of commercialization and are cheap and accessible; the compound is short in preparation route, simple and convenient in method and low in production cost, and provides more efficient and safe candidate medicines for clinical antimicrobial treatment. R1, R2, R3, R4, R5, R6, R7 and X in the general molecular formula are defined in the claim.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to a quinolone benzimidazole compound, a preparation method of the compound and an application in pharmacy. Background technique [0002] Quinolones antibacterial drugs are synthetic antibacterial drugs. This type of compound has the advantages of broad antibacterial spectrum, high antibacterial activity, less toxic and side effects, unique mechanism of action, and low price, and is widely used in the treatment of infectious diseases caused by various pathogenic microorganisms. However, with the widespread and inappropriate use of quinolone antibacterial drugs, quinolone-resistant strains continue to emerge, and the problem of bacterial drug resistance is becoming more and more serious. Anti-infection therapy is facing severe challenges. Therefore, it is necessary to modify or modify the structure of quinolones to develop more efficient and safe antibacterial new drugs to solve...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12A61K31/496A61P31/04A61P31/10
CPCC07D401/12Y02A50/30
Inventor 周成合张玲
Owner SOUTHWEST UNIV
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