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Quinolone thiazole compound and preparation method and application thereof

A quinolone thiazole and quinolone technology, applied in the field of chemistry, can solve problems such as toxic and side reactions, achieve the effects of high synthesis yield, easy availability of raw materials, and solving drug resistance

Active Publication Date: 2015-04-22
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, with the large-scale clinical use of such drugs, many toxic and side effects such as gastrointestinal reactions, anaphylactic shock, abnormal liver function, and renal failure have appeared.

Method used

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  • Quinolone thiazole compound and preparation method and application thereof
  • Quinolone thiazole compound and preparation method and application thereof
  • Quinolone thiazole compound and preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0026] The preparation of the compound represented by the general formula II: take ethyl acetoacetate and triethyl orthoformate as raw materials to undergo nucleophilic substitution reaction to obtain an intermediate, and then use diphenyl ether as a solvent to obtain 3- The quinolone ring with the acetyl group, followed by triethylamine as the catalyst and dimethyl sulfoxide as the solvent, undergoes nucleophilic substitution on the benzene ring at 120°C to obtain the intermediate of the secondary amine substituent, and then uses the basic catalyst DMF Reaction with ethyl bromide or cyclopropyl bromide as a solvent at 100°C to obtain the corresponding intermediate, and then brominated under the condition of acetic acid as a solvent to obtain the compound represented by the general formula II.

[0027]

Embodiment 1

[0028] Embodiment 1, the preparation of compound I-1

[0029]

[0030] In a 100mL round-bottomed flask, compound II-1 (0.33g, 1mmol), thiourea (0.076g, 1mmol) and ethanol (30mL) were stirred and reacted at 60°C for 3h under temperature control, cooled to room temperature, and traced by TLC to After the reaction was completed, 0.246 g was obtained by concentration, extraction, column chromatography separation, recrystallization and drying, with a yield of 80.0%. Wherein compound II-1: R is ethyl, R1 is fluorine, R2 is hydrogen; R3 is fluorine.

[0031] Compound I-1: yellow powder; melting point: 240-242°C; IR (KBr, cm -1 )ν: 3423(N-H), 3170(Ar-H), 3051(=C-H), 2989, 2865(CH 2 ,CH 3 ), 1656 (C=O), 1609, 1580, 1501, (aromatic frame); 1 H NMR (600MHz, CDCl 3 , ppm) δ8.59 (s, quinolone-2-H, 1H), 8.09 (d, J=7.5Hz, quinolone-5-H, 1H), 7.94 (s, thiazole-5-H, 1H), 7.18 (ddd, J=14.1,7.5,2.7Hz,quinolone-7-H,1H),4.98(s,thiazole-2-NH 2 ,2H),4.43(tt,J=6.9,3.5Hz,CH 2 CH 3 ,2H),1.5...

Embodiment 2

[0032] Embodiment 2, the preparation of compound 1-2

[0033]

[0034] In a 100mL round-bottomed flask, compound II-2 (0.33g, 1mmol), thiourea (0.076g, 1mmol) and ethanol (30mL) were stirred and reacted at 60°C for 3h under temperature control, cooled to room temperature, and traced by TLC to After the reaction was completed, 0.261 g was obtained by concentration, extraction, column chromatography separation, recrystallization and drying, with a yield of 85.1%. Wherein compound II-2: R is ethyl, R1 is fluorine, R2 is fluorine; R3 is hydrogen.

[0035] Compound I-2: yellow powder; melting point: 238-240°C; IR (KBr, cm -1 )ν: 3420(N-H), 3170(Ar-H), 3050(=C-H), 2995, 2865(CH 2 ,CH 3 ), 1655 (C=O), 1609, 1580, 1501, (aromatic frame); 1 H NMR (600MHz, CDCl 3 ,ppm): δ8.64(s,quinolone-2-H,1H),8.35(dd,J=10.7,9.0Hz,quinolone-5-H,1H),7.95(s,thiazole-5-H,1H ), 7.31–7.27 (m, quinolone-8-H, 1H), 4.85 (s, thiazole-2-NH 2 ,2H),4.23(q,J=7.3Hz,CH 2 CH 3 ,2H),1.55(t,J=7.2Hz,CH 2 CH...

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PUM

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Abstract

The invention discloses a quinolone thiazole compound as shown in the formula I and medicinal salt thereof, and further discloses a preparation method of the compound. Ethyl acetoacetate and triethyl orthoformate are used as raw materials to be subjected to multi-step reactions to obtain a quinolone ring with three-position acetyl, then bromization is conducted under the condition that acetic acid is used as solvent, and the acetic acid is reacted with thiourea so that the compound as shown in the formula I can be obtained. The quinolone thiazole compound has a certain inhibitory activity effect on gram positive bacteria and gram negative bacteria, and the method can be used for preparing antibacterial drugs (please see the formula in the specification).

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 have been widely used in the past few decades because of their advantages such as broad antibacterial spectrum, high antibacterial activity, less toxic and side effects, unique mechanism of action, significant oral effect, good pharmacokinetics, mature synthesis process, and low price. The treatment of infectious diseases caused by various pathogenic microorganisms is the most widely used synthetic anti-infective drug in the world after cephalosporin antibiotics. However, due to the widespread use and even abuse of quinolones in recent years, a large number of quinolone-resistant strains have appeared clinically. In addition, with the extensive clinical use of such drugs, numerous toxic and side effects such as gastrointestinal reactions...

Claims

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Application Information

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IPC IPC(8): C07D417/04A61K31/4709A61K31/5377A61K31/496A61P31/04
CPCC07D417/04Y02A50/30
Inventor 周成合崔胜峰阿德拉·迪内希
Owner SOUTHWEST UNIVERSITY
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