86483-51-4

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 28, p. 1558, 1985 DOI: 10.1021/jm00149a003

InChI:InChI=1/C11H9Cl2FO3/c1-2-17-11(16)5-10(15)6-3-9(14)8(13)4-7(6)12/h3-4H,2,5H2,1H3

Upstream product

• 86483-50-3 diethyl 2,4-dichloro-5-fluoro-benzoyl-malonate 
• 704-10-9 2,4-dichloro-5-fluoroacetophenone 
• 105-58-8 Diethyl carbonate 
• 86393-34-2 2,4-dichloro-5-fluorobenzoyl chloride 

Downstream Products

• 105460-29-5 methyl 2-(2,4-dichloro-5-fluorobenzoyl)-2-(2-pyrrolidylidene)-acetate 
• 105460-08-0 ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-2-(2-pyrrolidylidene)-acetate 
• 129527-46-4 ethyl 2,4-dichloro-5-fluoro-α-(2,4-difluorophenylhydrazono)benzoylacetate 
• 116885-09-7 ethyl 2-diazo-3-(2,4-dichloro-5-fluorophenyl)-3-oxopropionate 
• 109308-97-6 ethyl 3-N-formyl-N-methylhydrazyl-2-(2,4-dichloro-5-fluoro)benzoylacrylate 
• 86483-52-5 2,4-dichloro-alpha(elhoxymethlene)-5-fluoro-beta-oxo-benzene propanoic acid ethyl ester 
• 104600-41-1 3-(2,4-dichloro-5-fluorophenyl)-3-oxo-2-ethoxymethylenepropanoic acid ethyl ester 
• 114610-30-9 ethyl 2,4-dichloro-5-fluoro-α-(4-fluorophenylhydrazono)benzoylacetate 
• 98106-33-3 7-(4-Dimethylamino-piperidin-1-yl)-6-fluoro-1-(4-fluoro-phenyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 98106-24-2 1-(2,4-Difluoro-phenyl)-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 98106-18-4 1-(4-Bromo-phenyl)-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 98106-19-5 1-(4-Chloro-phenyl)-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 98106-20-8 6-Fluoro-1-(4-hydroxyphenyl)-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 98106-16-2 6-Fluoro-1-(3-fluoro-phenyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 

Relevant academic research and scientific papers

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.

Compounds with antibacterial and antiparasitic properties

There are provided novel compounds which have both antibacterial and antiparasitic properties, thereby reducing the need for using several compounds in combined antibacterial and antiparasitic treatment of livestock. The present novel compounds are especially well suited for treatment of coccidiosis, and they are represented by general formula (I) wherein R1-R6, X and A are as defined in the specification.

Pyridinyl-quinolone compounds, their preparation and use

Fluorinated 1-cyclopropyl-7-(substituted-pyridinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids of the formula STR1 wherein R is hydrogen, R' and R" are hydrogen or fluoro, or other groups and Z is 3- or 4-pyridinyl substituted by alkyl groups or substituted alkyl groups, are superior antibacterial agents. They are prepared via a coupling reaction between the corresponding esters (R=alkyl) having a halo group in the 7-position and a substituted (trialkylstannyl)pyridine.

7-(substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids

7-(substituted)piperazinyl-1-ethyl-6-fluoro-4-oxo-3-quinolinecarboxylic acids, the pharmacologically acceptable salts thereof, compositions containing them, processes and intermediates for producing them, and methods of using them to treat bacterial infections in warm-blooded animals.

Cycloaracylation of Enamines, I. - Synthesis of 4-Quinolone-3-carboxylic Acids

Starting with o-halobenzoyl chlorides 4 and open-chain secondary enamines 5, a new synthesis of 4-quinolone-3-carboxylic acids 12 is described.The reaction of 7-haloquinolone-3-carboxylic acids 12a-k with aliphatic amines 14 produces highly active antibacterial 7-aminoquinolone-3-carboxylic acids 15.The main product of the 1-cyclopropyl series, "ciprofloxacin" (15a), is being developed as a broad-spectrum chemotherapeutic agent.

Bactericidal agents

A method of combating plant-pathogenic bacteria, comprising applying to the bacteria or to a bacteria habitat a bactericidally effective amount of a cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid derivative of the formula STR1 in which A represents straight-chain or branched alkylene with 1 to 6 carbon atoms or a >C=CH-- radical, R1 represents alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, carboxyl, optionally substituted carbamoyl, cyano or dialkoxyphosphonyl or alkylsulphonyl with 1 to 4 carbon atoms in the alkyl part, and R2 represents hydrogen, alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, optionally substituted carbamoyl, cyano, chlorine, acetyl, alkyl with 1 to 3 carbon atoms or phenyl, or R1 and R2, together with the carbon atom which they substitute, can also form a 2-oxo-tetrahydrofuryl ring, R3, R4, R5 and R6 can be identical or different and represent hydrogen, methyl, ethyl or n- or i-propyl and X represents hydrogen, halogen or nitro, or an acid addition salt, alkali metal salt, alkaline earth metal salt, heavy metal salt or hydrate thereof. The heavy metal salts are new.

Microbicidal agents based on quinolonecarboxylic acid

Combating microorganisms, particularly in agriculture, with a 1-cyclopropyl-1,4-dihydro-4-oxo-quinolinecarboxylic acid of the formula STR1 in which R1 is hydrogen, fluorine, chlorine, bromine or nitro, R2 is hydrogen, chlorine, fluorine or the group STR2 particularly a 4-piperazinyl radical, or an acid addition, alkali metal, alkaline earth metal or heavy metal salt thereof which is tolerated by plants, or a hydrate thereof. Some of the compounds are known.

Preparation of halogenated aroylacetic acid esters

A process for the preparation of a halogenated aroylacetic acid ester of the formula STR1 in which R is alkyl with 1-6 carbon atoms, X and X2 each independently is halogen, and X1 and X3 each independently is hydrogen or h

Synthesis and Structure-Activity Relationships of Novel Arylfluoroquinolone Antibacterial Agents

A series of novel arylfluoroquinolones has been prepared.These derivatives are characterized by having a fluorine atom at the 6-position, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position.Structure-activity relationship (SAR) studies indicate that the in vitro antibacterial potency is greatest when the 1-substituent is either p-fluorophenyl or p-hydroxyphenyl and the 7-substituent is either 1-piperazinyl, 4-methyl-1-piperazinyl, or 3-amino-1-pyrrolidinyl.The electronic and spatial properties of the 1-substituent, as well as the steric bulk, play important roles in the antimicrobial potency in this class of antibacterials.As a result of this study, compounds 45 and 41 were found to possess excellent in vitro potency and in vivo efficacy.