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Ferrocene-quinolone amide compound as well as preparation method and application thereof

A quinolone amide, ferrocene technology, applied in chemical instruments and methods, metallocene, organic chemistry and other directions, can solve the problems such as the biological activity of ferrocene-quinolone amide compounds that have not yet been seen, and achieve a simple and easy-to-operate synthesis method. , obvious inhibitory effect

Inactive Publication Date: 2015-07-22
GUILIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no relevant reports on the ferrocene-quinolone amide compounds obtained by hybridizing the quinolone structure with the ferrocene pharmacophore and their biological activities.

Method used

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  • Ferrocene-quinolone amide compound as well as preparation method and application thereof
  • Ferrocene-quinolone amide compound as well as preparation method and application thereof
  • Ferrocene-quinolone amide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Preparation of ciprofloxacin methyl ester (compound 2a)

[0034] In the flask, add 1.35g (4mmol) of ciprofloxacin, 50mL of methanol, slowly add 2mL of concentrated sulfuric acid dropwise, reflux for 24h, evaporate most of the solvent, adjust the pH to 9 with saturated sodium bicarbonate solution, and then use CH 2 Cl 2 (3×20mL) Extract, combine the organic layers, wash with water to pH 8, and use anhydrous Na for the organic layer 2 SO 4 Dry for several hours, filter, evaporate the solvent under reduced pressure and use silica gel column chromatography (eluent is V (Methanol) : V (Dichloromethane) = 1:10) Purified to obtain 0.704 g of methyl ciprofloxacin (white solid), with a yield of 51%, and a melting point of 253-254°C.

[0035] With reference to the method of Example 1 above, other methyl esters of floxacin (norfloxacin methyl ester, enoxacin methyl ester, clinfloxacin methyl ester) were prepared as follows:

[0036] Repeat Example 1, the difference is: ① repl...

Embodiment 2

[0039] Example 2: Preparation of ferrocene carbonyl chloride (compound 3)

[0040] Add 4.6g (0.02mmol) of dry ferrocene formic acid and 80mL of anhydrous benzene into a three-necked flask. Under the protection of nitrogen, slowly add 6.24g (0.03mmol) of phosphorus pentachloride in several times, stir at room temperature for 3h, and reduce pressure. The benzene was distilled off, and petroleum ether (60-90°C) was extracted to obtain a dark red solution, which was distilled under reduced pressure and cooled to precipitate dark red needle-like crystals. The yield was 80%, mp: 48-49°C.

Embodiment 3

[0041] Example 3: (7-(4-ferrocenecarbonyl-piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methyl ester (chemical name: Preparation of 7-(4-ferrocenyl piperazinyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinolone-3-carboxylic acid methyl ester) (Compound 4a)

[0042]

[0043] Add 0.345 g (1 mmol) of ciprofloxacin methyl ester, 15 mL of anhydrous THF, 0.4 mL of triethylamine, and nitrogen protection in a dry double-necked flask. Stir under an ice water bath. Use a syringe to slowly inject 5 mL of ferrocene formyl chloride ( 1.2mmol) in anhydrous THF solution, after 10 minutes, transfer to room temperature and stir for 24h, and then filter with suction to obtain compound 4a (if not pure, use silica gel column chromatography (eluent is V (Methanol) : V (Dichloromethane) = 1:20) Purification). Yellow solid, mp: 186~189℃, yield 72%. IR(KBr)v / cm -1 : 3450.20,1725.72,1619.44,1480.06,1443.05,1384.21,1332.78,1258.77,1169.55,1105.32,1011.04,932.58,80...

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Abstract

The invention discloses a series of ferrocene-quinolone amide compounds as well as a preparation method and application thereof. The preparation method comprises the following steps: 1) selecting quinolone bulk drug according to a target compound to be prepared, placing the selected quinolone bulk drug and methyl alcohol in a reactor to be subjected to reflux reaction, adjusting the pH of the reaction liquid to be 8-10, then, extracting by using an extraction agent, collecting an organic phase, and removing the solvent through evaporation, so as to obtain corresponding floxacin methyl ester; 2) taking the floxacin methyl ester and triethylamine, placing the floxacin methyl ester and triethylamine in a first organic solvent, and adding chlorocarbonyl ferrocene for reaction under the protection of inert gas, and performing suction filtration, so as to obtain an intermediate body; 3) taking the intermediate body and an alkaline substance, dissolving the intermediate body and the alkaline substance with a second organic solvent, performing reflux reaction, adjusting the pH of the reaction liquid to be 1-4, filtering, and collecting sediments, so as to obtain the target compound. The compound provided by the invention has obvious inhibiting effect on certain bacteria, and is expected to be used for preparing antibacterial drug.

Description

Technical field [0001] The invention relates to a ferrocene-quinolone hybrid compound, in particular to a class of ferrocene-quinolone amide compounds and a preparation method and application thereof. Background technique [0002] Quinolones have become a broad-spectrum, high-efficiency and low-toxicity synthetic antibacterial drug widely used clinically, mainly used to treat systemic diseases such as gastrointestinal tract, urinary tract and respiratory tract caused by bacterial infection. [1-2] However, with the further expansion of the use of quinolone drugs, the phenomenon of bacterial resistance to drugs has become increasingly serious [3] At the same time, the toxicity of some fluoroquinolones to the cardiovascular system, central nervous system, liver and kidney tissues of the users has also received widespread attention. [4-5] , The continuous development of new oxolone antibacterial drugs with broader antibacterial spectrum, higher efficacy, stronger selectivity, lower sid...

Claims

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Application Information

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IPC IPC(8): C07F17/02A61P31/04
CPCC07F17/02
Inventor 黄婉云廖迎彭湘艳殷鹏龙廖月英
Owner GUILIN MEDICAL UNIVERSITY
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