16600-22-9

Usage

Uses

Used in Pharmaceutical Industry:
7-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID METHYL ESTER is used as an antibiotic for treating bacterial infections due to its broad-spectrum activity and ability to inhibit the DNA gyrase enzyme, which is essential for bacterial DNA replication.
Used in Antibacterial Drug Development:
7-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID METHYL ESTER is used as a key component in the development of new antimicrobial drugs, addressing the growing need for effective treatments against antibiotic-resistant bacteria. Its unique mechanism of action and broad-spectrum efficacy make it a promising candidate for pharmaceutical research and development.

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

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

Downstream Products

• 86-47-5 4-hydroxy-7-chloro-3-quinoline-carboxylic acid 
• 111826-39-2 N-(α-methyl-α-carbethoxy-β-phenethyl)-7-chloro-4-hydroxyquinoline-3-carboxamide 
• 111826-38-1 N-(α-methyl-β-phenethyl)-7-chloro-4-hydroxyquinoline-3-carboxamide 
• 19499-19-5 4,7-dichloroquinoline-3-carboxylic acid ethyl ester 
• 86-99-7 7-chloro-4-hydroxylquinoline 
• 86-98-6 4,7-dichloroquinoline 
• 5407-57-8 N-(7-chloroquinolin-4-yl)ethylenediamine 
• 54-05-7 Chloroquine 
• 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 

Relevant academic research and scientific papers

COMPOUNDS FOR THE DEGRADATION OF BRD9 OR MTH1

Compounds that degrade BRD9 or MTH1 via the ubiquitin proteasome pathway in a subject in need thereof for therapeutic applications are provided. The compounds provided have an E3 Ubiquitin Ligase targeting moiety (Degron) that is linked to a Targeting Ligand for BRD9 or MTH1.

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)

Dichloro-4-quinolinol-3-carboxylic acid: Synthesis and antioxidant abilities to scavenge radicals and to protect methyl linoleate and DNA

5,7-, 5,8-, 6,8-, 7,8-Dichloro-4-quinolinol-3-carboxylic acid (5,7-, 5,8-, 6,8-, 7,8-DCQA) together with 7-chloro-4-quinolinol-3-carboxylic acid (7-CQA) and 4-quinolinol-3-carboxylic acid (QA) were synthesized to investigate the antioxidant properties. 5,7-DCQA exhibited the highest ability to scavenge 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+.), 2,2′-diphenyl-1-picrylhydrazyl (DPPH) and galvinoxyl radicals. 6,8-DCQA possessed the highest efficacy to protect methyl linoleate against 2,2′-azobis(2-amidinopropane)dihydrochloride (AAPH)-induced oxidation. 5,7-, 5,8-DCQA and QA were able to retard the β-carotene-bleaching in β-carotene-linoleic acid emulsion. In addition, 5,8- and 6,8-DCQA efficiently protected DNA against hydroxyl radical (.OH)-mediated oxidation, and 5,8-DCQA and 7-CQA were active to protect DNA against AAPH-induced oxidation. Furthermore, only 7-CQA can protect DNA against Cu2+/glutathione (GSH)-mediated oxidation. Dichloro-4-quinolinol-3-carboxylic acids were potent to be antiradical drugs, and were worthy to be researched pharmacologically.

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.

Design, synthesis, and biological evaluation of novel 4-hydro-quinoline-3- carboxamide derivatives as an immunomodulator

A series of novel quinoline-3-carboxamide derivatives were synthesized and evaluated for their immunomodulatory activity. The compounds were tested in vitro for effects on spleen lymphocyte proliferation and TNF-α production by macrophage. Three compounds showed immunomodulatory profiles similar to and more potent than those of linomide and FR137316 and were selected for further pharmacological studies in vivo.

Structure-activity relationship investigations of the modulating effect of core substituents on the affinity of pyrazoloquinolinone congeners for the benzodiazepine receptor

A series of 6- and 7-substituted-2-arylpyrazolo [4,3-c] quinolin-3-ones was synthesized and tested in vitro for binding with the benzodiazepine receptor in competition with [3H]flunitrazepam. Electronic parameters (molecular electrostatic potential (MEP), charge distribution on the nitrogen atoms, dipole moment μ, and ionization potential (IP) were calculated for the compounds by semi-empirical quantum chemistry methods. Lipophilicity of the compounds, expressed as logarithm of the octanol-water partition coefficient (log P), was calculated by the program Pallas. A quantitative correlation of the biological data with molecular parameters revealed a significant dependence (r = 0.95) of the activity on hydrophobic constants of the substituents, log P, and magnitude of the MEP minimum associated with the carbonyl oxygen atom.

Antimalarials: Synthesis of 4-aminoquinolines that circumvent drug resistance in malaria parasites

The strategies described here have permitted the synthesis of a series of 4-aminoquinoline antimalarials. Substantive improvements over previous syntheses include nucleophilic substitution with neat amine rather than in phenol, regioselective reductive alkylation to convert the terminal primary amine (12a-20a) on the diaminoalkane side chain to a diethylamino group, and purification by column chromatography with basic alumina. The 1H nmr spectra obtained after regioselective reductive alkylation with sodium borodeuteride (in comparison with sodium borohydride) demonstrated that this reductive alkylation proceeds via formation and subsequent reduction of the corresponding diamides in situ.