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Quinolone azole alcohol compounds as well as preparation method and application thereof

A technology of quinolazolol and quinolones, which is applied in the field of chemistry, can solve the problems of serious bacterial drug resistance, etc., and achieve the effects of solving drug resistance, easy-to-obtain raw materials, and simple preparation methods

Active Publication Date: 2014-10-08
SOUTHWEST UNIVERSITY
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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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  • Quinolone azole alcohol compounds as well as preparation method and application thereof
  • Quinolone azole alcohol compounds as well as preparation method and application thereof
  • Quinolone azole alcohol compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1, the preparation of compound II-1

[0035]

[0036] In a 100mL round bottom flask, norfloxacin hydrochloride (0.96g, 0.0027mol), sodium bicarbonate (0.69g, 0.0048mol) and an appropriate amount of acetonitrile were stirred at a temperature of 50°C for 0.5h, cooled to room temperature, and added to the ring Oxychloropropane (1.00g, 0.0027mol) was kept under temperature control at 45°C and continued to stir, followed by thin-layer chromatography until the end of the reaction, and then concentrated, extracted, separated by column chromatography, recrystallized, and dried to obtain 0.68g of compound II-1. The yield was 67.4%.

[0037] Compound II-1: white powder; melting point 185-186°C; 1 H NMR (300MHz, CDCl 3 ):δ15.05(s,1H,COOH),8.63(s,1H,quinolone2-H),7.99(d,J=13.0Hz,1H,quinolone5-H),6.80(d,J=6.8Hz,1H ,quinolone8-H), 4.53(t, J=8.3Hz, 1H, CH 2 ), 4.30 (dd,2H,quinolone N-CH 2 ), 3.59(t, J=5.0Hz, 1H, O-CH), 3.32(t, J=14.3Hz, 4H, piperazine N-CH 2 ), 2.8...

Embodiment 2

[0038] Embodiment 2, the preparation of compound II-2

[0039]

[0040]In a 100mL round bottom flask, ciprofloxacin hydrochloride (0.99g, 0.0027mol), sodium bicarbonate (0.69g, 0.0048mol) and appropriate amount of acetonitrile were stirred at 50°C for 0.5h, cooled to room temperature, and added to Oxychloropropane (1.00g, 0.0027mol) was kept under temperature control at 45°C and continued to stir, followed by thin-layer chromatography until the end of the reaction, and then concentrated, extracted, separated by column chromatography, recrystallized, and dried to obtain 0.67g of compound II-2. The yield was 64.0%.

[0041] Compound II-2: yellow powder; melting point 200-202°C; 1 H NMR (600MHz, DMSO-d 6 ): δ15.19(s,1H,COOH),8.63(s,1H,quinolone2-H),7.85(dd,J=10.9,7.6Hz,1H,quinolone5-H),7.54(d,J=6.1Hz ,1H,quinolone8-H),5.13(d,J=4.5Hz,1H,quinolone N-CH),3.91(td,J=9.9,4.8Hz,1H,O-C-H),3.81(s,2H,O-CH 2 ),3.71-3.58(m,4H,piperazine N-CH 2 ), 2.67 (td, J=10.9, 6.3Hz, 4H, piperazi...

Embodiment 3

[0042] Embodiment 3, the preparation of compound II-3

[0043]

[0044] In a 100mL round bottom flask, Clinfloxacin hydrochloride (5.00g, 0.0137mol), sodium bicarbonate (4.60g, 0.0548mol) and an appropriate amount of ethanol were stirred at a temperature of 50°C for 0.5h, cooled to room temperature, and epoxy chloride was added. Propane (2.50g, 0.0274mol) was kept under temperature control at 45°C and continued stirring, tracked by thin-layer chromatography until the end of the reaction, and then concentrated, extracted, separated by column chromatography, recrystallized, and dried to obtain 3.61g of compound II-3, with a yield of 62.4% .

[0045] Compound II-3: yellow powder; melting point 191-192°C; 1 H NMR (600MHz, DMSO-d 6 ):δ14.56(s,1H,COOH),8.83(s,1H,quinolone2-H),7.93(d,J=11.9Hz,1H,quinolone5-H),4.42-4.37(m,1H,NH- CH 2 ),3.92-3.86(m,1H,NH-CH 2 ), 3.70(dd, J=11.0, 4.1Hz, 1H, cyclopropyl-CH), 3.60(dd, J=11.0, 5.5Hz, 1H, O-C-H), 3.34(s, 4H, pyrrole N-CH 2 ), 2.63 ...

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Abstract

The invention discloses quinolone azole alcohol compounds which are shown in a general formula (I) and the structure of an intermediate (II) and has antimicrobial activity and a preparation method of pharmaceutically acceptable salts of the compounds. The invention also relates to application of the quinolone azole alcohol compounds and salts thereof as anti-infection medicines. According to the invention, the related preparation raw materials are high in commercialization degree, cheap and easily available, the preparation route is short, and the preparation method is simple and convenient. The quinolone azole alcohol compounds have certain inhibitory activity to gram-positive bacteria, gram-negative bacteria and fungi and can be used for preparing an antibacterial and / or antifungal drug. R1, R2, R3, R4, X and Im in the general molecular formula are defined in the claims.

Description

technical field [0001] The invention belongs to the field of chemistry, relates to a new class of organic compound, and also relates to the preparation method and medical application of the compound. 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 clini...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D401/14C07D471/04A61K31/4709A61K31/496A61K31/4375A61P31/04A61P31/10
CPCC07D401/12C07D401/14C07D471/04Y02A50/30
Inventor 周成合张玲
Owner SOUTHWEST UNIVERSITY
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