96568-04-6

Usage

Chemical Properties

Off-White Solid

Uses

Enoxacin intermediate.

General Description

Ethyl 2,6-dichloro-5-fluoro-β-oxo-3-pyridinepropionate is a β-keto ester.

InChI:InChI=1/C10H8Cl2FNO3/c1-2-17-8(16)4-7(15)5-3-6(13)10(12)14-9(5)11/h3H,2,4H2,1H3

Upstream product

• 1071-46-1 hydrogen ethyl malonate 
• 96568-02-4 2,6-dichloro-5-fluoro-3-nicotinoyl chloride 
• 6148-64-7 ethyl potassium malonate 
• 82671-02-1 2,6-dichloro-5-fluoro-pyridine-3-carbonitrile 
• 113237-18-6 5-fluoro-2,6-dihydroxynicotinonitrile 
• 120876-32-6 ethyl 2-diazo-3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate 
• 113237-20-0 2,6-dichloro-5-fluoropyridine-3-carboxamide 
• 82671-03-2 ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate 
• 82671-06-5 2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid 
• 120876-33-7 ethyl 2-hydrazono-2-(2,6-dichloro-5-fluoronicotinoyl)acetate 
• 96568-03-5 diethyl (2,6-dichloro-5-fluoro-pyridine-3-carbonyl)-malonate 
• 35227-78-2 diethyl (ethoxymagnesio)malonate 

Downstream Products

• 130878-52-3 Ethyl 1-cyclopropyl-2-phenylthio-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 
• 100490-99-1 ethyl-3,1-(2,4-difluoroanilino)-2-(2,6-dichloro-5-fluoronicotinyl) acrylate 
• 100361-18-0 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid 
• 100491-00-7 ethyl 3-p-fluoroanilino-2-(2,6-dichloro-5-fluoronicotinyl)acrylate 
• 100426-73-1 (Z)-2-(2,6-Dichloro-5-fluoro-pyridine-3-carbonyl)-3-phenylamino-acrylic acid ethyl ester 
• 110286-57-2 7-chloro-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 767306-94-5 7-chloro-6-fluoro-1-(4-hydroxy-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid 
• 100491-40-5 7-chloro-6-fluoro-1-(4-methoxy-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 767306-90-1 (Z)-2-(2,6-Dichloro-5-fluoro-pyridine-3-carbonyl)-3-(4-methoxy-phenylamino)-acrylic acid ethyl ester 
• 1025982-33-5 6-fluoro-1-(4-methoxy-phenyl)-4-oxo-7-piperazin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid 
• 1026719-54-9 6-fluoro-1-(4-methoxy-phenyl)-4-oxo-7-piperazin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 1027237-49-5 7-((3R,5S)-3,5-Dimethyl-piperazin-1-yl)-6-fluoro-1-(4-methoxy-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid 
• 1027739-66-7 7-((3R,5S)-3,5-Dimethyl-piperazin-1-yl)-6-fluoro-1-(4-methoxy-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis, antimycobacterial and antibacterial activity of 1-(6-amino-3,5-difluoropyridin-2-yl)fluoroquinolone derivatives containing an oxime functional moiety

A series of novel 1-(6-amino-3,5-difluoropyridin-2-yl)fluoroquinolone derivatives containing an oxime functional moiety were synthesized and evaluated for their biological activity. Our results reveal that compounds 9a-9c have considerable activity against both of MTB H37Rv ATCC 27294 (MICs: 3.81-7.13 μg/mL) and methicillin-sensitive Staphylococcus aureus strains (MICs: 0.008-0.5 μg/mL).

ANTIVIRAL AND ANTIMICROBIAL COMPOUNDS

Disclosed are guanidine and biguanidine derivatives which have anti-viral and antibacterial activity. Also disclosed are pharmaceutical compositions containing such compounds as an active ingredient, and anti-viral and anti-bacterial methods utilizing such compounds. Methods of treating infections using the guanidine and biguanidine derivatives are also disclosed.

1,8-Naphthyridine-3-carboxamide derivatives with anticancer and anti-inflammatory activity

A number of 1-propargyl-1,8-naphthyridine-3-carboxamide derivatives (15-35) have been synthesized and screened for their in vitro cytotoxicity and anti-inflammatory activity. Compounds 22, 31 and 34 have shown high cytotoxicity against a number of cancer cell lines, while compound 24 showed significant anti-inflammatory activity.

Process for Preparing Beta-Ketoester Compounds

The present invention relates to a process for preparing a beta-keto ester compound of formula (1), which is an intermediate for the synthesis of quinolone antibiotics. Particularly, the present invention is characterized by the reaction of an organo nitrile compound with a salt of mono-alkyl malonate in the presence of metal salt, and so the reaction is easy to control due to its endothermic nature, and is devoid of lachrymatory reagents with excellent reproducibility. Subsequent in situ hydrolysis in the presence of aqueous acid solution provided the compound of formula (1).

A PROCESS FOR PREPARING BETA-KETOESTER COMPOUNDS

The present invention relates to a process for preparing a beta-keto ester compound of formula (1) , which is an intermediate for the synthesis of quinolone antibiotics. Particularly, the present invention is characterized by the reaction of an organo nitrile compound with a salt of mono-alkyl malonate in the presence of metal salt, and so the reaction is easy to control due to its endothermic nature, and is devoid of lachrymatory reagents with excellent reproducibility. Subsequent in situ hydrolysis in the presence of aqueous acid solution provided the compound of formula (1).

Discovery of the decarboxylative biaise reaction and its application to the efficient synthesis of ethyl 2,6-dichloro-5-fluoronicotinoylacetate

An efficient synthesis of 2,6-dichloro-5-fluoronicotinoylacetate (1) has been accomplished in a single step using the unprecedented decarboxylative Biaise reaction of 3-cyano-2,6-dichloro-5-fluoropyridine (4) with potassium ethyl malonate in the presence of zinc chloride.

ANTIMICROBIAL QUINOLONES, THEIR COMPOSITIONS AND USES

Compounds of the following formula (I) are effective antimicrobial agents.

A safe, economical method for the preparation of β-oxo esters

A high yield, economical method for preparation of β-oxo esters has been developed involving the reaction of acid chlorides with potassium ethyl malonate using a magnesium chloride-triethylamine base system in either acetonitrile or ethyl acetate solvents. The method is suitable for the preparation of high purity β-oxo esters in the laboratory and also in large scale production.

Fluoronaphthyridines as Antibacterial Agents. 4. Synthesis and Structure-Activity Relationships of 5-Substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acids

A series of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for their in vitro and in vivo antibacterial activities.The 5-methyl group gave better in vitro activity with the 1-cyclopropyl appendage, but poorer activity with the 1-tert-butyl moiety.With the 1-(2,4-difluorophenyl) substitution, the influence of the 7-cycloalkylamino group was determinant: a (3S)-3-aminopyrrolidine was shown to enhance greatly the in vitro and in vivo activity of the 5-methyl derivative.Compound 33 (BMY 43748) was selec ted as a promising candidate for an improved therapeutic agent.