19499-19-5

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 4,7-DICHLOROQUINOLINE-3-CARBOXYLATE is used as a key intermediate in the synthesis of various antitumor agents. Its chemical structure allows for the development of new compounds with potential抗癌 (antitumor) activities, which can be beneficial in the treatment of cancer.
Used in the Preparation of SAR of (Morpholine)carbonyland (Ethoxycarbonyl)anilinoquinolines:
ETHYL 4,7-DICHLOROQUINOLINE-3-CARBOXYLATE serves as a starting material for the synthesis of (morpholine)carbonyland (ethoxycarbonyl)anilinoquinolines. These synthesized compounds are useful in the treatment of cancer, as they can exhibit selective toxicity towards cancer cells while sparing normal cells. The study of their structure-activity relationship (SAR) can provide valuable insights into the design of more effective and targeted cancer therapies.

Upstream product

• 16600-22-9 7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester 
• 3412-99-5 2-(3-chlorophenylamino)methylenemalonic acid diethyl ester 
• 40516-46-9 diethyl (ethoxymethylene)malonate 
• 54132-35-3 ethyl 7-chloro-1,4-dihydro-4-oxo-3-quinolinecarboxylate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 108-42-9 3-chloro-aniline 

Downstream Products

• 130373-06-7 4-(4-Butyl-phenylamino)-7-chloro-quinoline-3-carboxylic acid ethyl ester 
• 130373-07-8 4-(4-Butoxy-phenylamino)-7-chloro-quinoline-3-carboxylic acid ethyl ester 
• 96504-63-1 ethyl 7-chloro-4-(phenylamino)quinoline-3-carboxylate 
• 130373-09-0 7-chloro-4-(3-chloro-anilino)-quinoline-3-carboxylic acid ethyl ester 
• 49711-99-1 7-chloro-4-(2-methoxycarbonyl-anilino)-quinoline-3-carboxylic acid ethyl ester 
• 130373-04-5 7-Chloro-4-m-tolylamino-quinoline-3-carboxylic acid ethyl ester 
• 130373-05-6 7-Chloro-4-(2,3-dimethyl-phenylamino)-quinoline-3-carboxylic acid ethyl ester 
• 68262-44-2 ethyl 4-azido-7-chloroquinoline-3-carboxylate 
• 923585-78-8 7-chloro-4-[4-(3,3,4-trimethylpiperazin-1-yl)phenylamino]quinoline-3-carboxylic acid ethyl ester 
• 1000376-91-9 C₁₆H₁₆ClN₃O 
• 1222096-46-9 8-chloro[1,2,3]triazino[5,4-c]quinolin-4-ol 
• 630067-21-9 4,7-dichloroquinoline-3-carboxylic acid 
• 1373767-17-9 ethyl 2-([1,1'-biphenyl]-3-yl)-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 93989-50-5 7-Chlor-4-anilino-chinolin-carbonsaeure-⁽³⁾ 

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.

Defined concatenated α6α1β3γ2 GABAA receptor constructs reveal dual action of pyrazoloquinolinone allosteric modulators

Pyrazoloquinolinones (PQs) have been extensively studied as modulators of GABAA receptors with different subunit composition, exerting modulatory effects by binding at α+/β- interfaces of GABAA receptors. PQs with a substituent in position R7 have been reported to preferentially modulate α6- subunit containing GABAA receptors which are mostly expressed in the cerebellum but were also found in the olfactory bulb, in the cochlear nucleus, in the hippocampus and in the trigeminal sensory pathway. They are considered potentially interesting in the context of sensori-motor gating deficits, depressive-like behavior, migraine and orofacial pain. Here we explored the option to modify the lead ligands’ R7 position. In the compound series we observed two different patterns of allosteric modulation in recombinantly expressed α6β3γ2 receptors, namely monophasic and biphasic positive modulation. In the latter case the additional phase occurred in the nanomolar range, while all compounds displayed robust modulation in the micromolar range. Nanomolar, near silent binding has been reported to occur at benzodiazepine binding sites, but was not investigated at the diazepam insensitive α6+/γ2- interface. To clarify the mechanism underlying the biphasic effect we tested one of the compounds in concatenated receptors. In these constructs the subunits are covalently linked, allowing to form either the α6+/γ2- interface, or the α6+/β3- interface, to study the resulting modulation. With this approach we were able to ascribe the nanomolar modulation to the α6+/γ2- interface. While not all compounds display the nanomolar phase, the strong modulation at the α6+/β3 interface proved to be tolerant for all tested R7 groups. This provides the future option to introduce e.g. isotope labelled or fluorescent moieties or substituents that enhance solubility and bioavailability.

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)

Lead optimization of 3-carboxyl-4(1 H)-quinolones to deliver orally bioavailable antimalarials

Malaria is a protozoal parasitic disease that is widespread in tropical and subtropical regions of Africa, Asia, and the Americas and causes more than 800,000 deaths per year. The continuing emergence of multidrug-resistant Plasmodium falciparum drives the ongoing need for the development of new and effective antimalarial drugs. Our previous work has explored the preliminary structural optimization of 4(1H)-quinolone ester derivatives, a new series of antimalarials related to the endochins. Herein, we report the lead optimization of 4(1H)-quinolones with a focus on improving both antimalarial potency and bioavailability. These studies led to the development of orally efficacious antimalarials including quinolone analogue 20g, a promising candidate for further optimization.

New 1,8-naphthyridine and quinoline derivatives as CB2 selective agonists

A series of new 1,8-naphthyridine and quinoline derivatives were synthesized and evaluated for their cannabinoid receptor affinity. In particular, compounds 2, 5, 11, and 13 showed a high CB2 affinity and CB2 versus CB1 selectivity, in agreement with molecular modeling studies. Furthermore, compound 2 also exhibited in vivo antinociceptive effects.

Structure-activity relationship of quinoline derivatives as potent and selective α2c-adrenoceptor antagonists

Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human α2- adrenoceptor subtypes (α2A, α2B, and α2C). A number of compounds with good antagonist potencies against the α2C-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl)phenylamino]quinolin-3-yl}methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the α2c-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the α2C- adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

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.

Imidazolylethoxy derivatives of quinoline-3-methanols

Imidazolylethoxy derivatives of quinoline-3-methanols having the general formula STR1 and their acid addition salts are useful as antifungal and antibacterial agents.