16600-22-9

Basic information

• Product Name: 7-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 7-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID METHYL ESTER;Ethyl7-chloro-4-hydroxy-3-quinolinecarboxylate;Ethyl-7-chloro-1,4-dihydro-4-oxo-3-quinolinecarboxylate;3-Quinolinecarboxylic acid, 7-chloro-4-hydroxy-, ethyl ester;3-Carbethoxy-4-hydroxy-7-chloroquinoline;NSC 403048;Ethyl 7-chloro-4-hydroxyquinoline-3-carboxylate;Ethyl 4-hydroxy-7-chloroquinoline-3-carboxylate
• CAS NO: 16600-22-9
• Molecular Formula: C₁₂H₁₀ClNO₃
• Molecular Weight: 237.64
• EINECS: -0
• Mol File: 16600-22-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 296-298℃
• Boiling Point: 378.4 °C at 760 mmHg
• Flash Point: 182.7 °C
• Appearance: /
• Density: 1.386
• Vapor Pressure: 6.3E-06mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.18±0.50(Predicted)
• CAS DataBase Reference: 7-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 7-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID METHYL ESTER(16600-22-9)
• EPA Substance Registry System: 7-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID METHYL ESTER(16600-22-9)

Safety Data

• Hazardous Substances Data: 16600-22-9(Hazardous Substances Data)

Usage

General Description

7-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID METHYL ESTER is a chemical compound that is a methyl ester derivative of 7-chloro-4-hydroxyquinoline-3-carboxylic acid. It is a quinolone antibiotic that is used to treat bacterial infections. This chemical compound has a broad spectrum of activity against both Gram-positive and Gram-negative bacteria. It works by inhibiting the DNA gyrase enzyme of bacteria, leading to the disruption of DNA replication and ultimately the death of the bacterial cells. 7-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID METHYL ESTER has potential applications in the pharmaceutical industry for the development of new antibiotics and antimicrobial drugs.

InChI:InChI=1/C12H10ClNO3/c1-2-17-12(16)9-6-14-10-5-7(13)3-4-8(10)11(9)15/h3-6H,2H2,1H3,(H,14,15)

Upstream product

• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 108-42-9 3-chloro-aniline 
• 105-53-3 diethyl malonate 
• 40516-46-9 diethyl (ethoxymethylene)malonate 
• 3412-99-5 2-(3-chlorophenylamino)methylenemalonic acid diethyl ester 
• 101-84-8 diphenylether 

Downstream Products

• 86-98-6 4,7-dichloroquinoline 
• 93989-50-5 7-Chlor-4-anilino-chinolin-carbonsaeure-⁽³⁾ 
• 49711-99-1 7-chloro-4-(2-methoxycarbonyl-anilino)-quinoline-3-carboxylic acid ethyl ester 
• 96504-63-1 ethyl 7-chloro-4-(phenylamino)quinoline-3-carboxylate 
• 130373-10-3 7-Chloro-4-(3-trifluoromethyl-phenylamino)-quinoline-3-carboxylic acid ethyl ester 
• 130373-07-8 4-(4-Butoxy-phenylamino)-7-chloro-quinoline-3-carboxylic acid ethyl ester 
• 130373-24-9 7-Chloro-4-(3-trifluoromethyl-phenylamino)-quinoline-3-carboxylic acid 
• 130373-06-7 4-(4-Butyl-phenylamino)-7-chloro-quinoline-3-carboxylic acid ethyl ester 
• 130373-05-6 7-Chloro-4-(2,3-dimethyl-phenylamino)-quinoline-3-carboxylic acid ethyl ester 
• 130373-21-6 4-(4-Butoxy-phenylamino)-7-chloro-quinoline-3-carboxylic acid 
• 130373-34-1 4-(2-Carboxy-phenylamino)-7-chloro-quinoline-3-carboxylic acid 
• 130373-20-5 4-(4-Butyl-phenylamino)-7-chloro-quinoline-3-carboxylic acid 
• 130373-04-5 7-Chloro-4-m-tolylamino-quinoline-3-carboxylic acid ethyl ester 
• 130373-19-2 7-Chloro-4-(2,3-dimethyl-phenylamino)-quinoline-3-carboxylic acid 

Relevant articles and documents

Synthesis method of 4,7-dichloroquinoline

The invention discloses a synthesis method of 4,7-dichloroquinoline. The synthesis method is characterized by comprising the following steps: synthesizing 7-chloro-4-hydroxylquinoline-3-carboxylic acid by using a one-pot method, and carrying out decarboxylation and chlorination on the 7-chloro-4-hydroxylquinoline-3-carboxylic acid to obtain 4,7-dichloroquinoline. The step of synthesizing the 7-chloro-4-hydroxylquinoline-3-carboxylic acid by the one-pot method comprises the following sub-steps: with m-chloroaniline, triethyl orthoformate or trimethyl orthoformate and diethyl malonate as raw materials, carrying out condensation under the catalysis of anhydrous ferric trichloride to obtain diethyl 2-[[(3-chlorophenyl)amino]methylene]malonate, directly adding a condensation reaction solution into an organic solvent, carrying out heating cyclization to obtain 7-chloro-4-hydroxylquinoline-3-carboxylic acid ethyl ester, and after the cyclization reaction is completed, adding sodium hydroxidefor hydrolysis to obtain 7-chloro-4-hydroxylquinoline-3-carboxylic acid. Although the whole process comprises five reactions, intermediate products are good enough in purity and can be directly synthesized into a target product without purification, so operation is easy and convenient and industrialization is facilitated; and raw materials are easily available, and pollution is small.

A four-ring quinolinone alkaloid derivative and its preparation method and application (by machine translation)

The invention relates to a four-ring quinolinone alkaloid derivative, or a tautomer thereof, stereo isomer, racemate, enantiomer of non-isometric mixture, geometric isomer, solvate, pharmaceutically acceptable salt or prodrug, and pharmaceutical composition containing the compound. The invention also discloses such compounds and pharmaceutical compositions thereof as a medicament, in particular as anti-virus, antibacterial and the anti-parasitic drug use. (by machine translation)

Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat-TAR interaction inhibitors

Thirty-two quinoline derivatives were designed and synthesized as HIV-1 Tat-TAR interaction inhibitors. All the compounds showed high antiviral activities in inhibiting the formation of SIV-induced syncytium in CEM174 cells. Nine of them with low cytotoxicities were evaluated by Tat dependent HIV-1 LTR-driven CAT gene expression colorimetric enzyme assay in human 293T cells, indicating effective inhibitory activities of blocking the Tat-TAR interaction. Molecular modeling experiments indicated that these compounds may inhibit Tat-TAR interaction by binding to Tat protein instead of TAR RNA.