150258-21-2

Usage

Uses

Used in Pharmaceutical Industry:
4,5,7-Trichloroquinoline-3-carboxylic acid ethyl ester is used as an intermediate in the synthesis of various pharmaceutical drugs. Its unique structure and properties make it a valuable building block in the development of new compounds with potential pharmacological applications.
Used in Agrochemical Industry:
4,5,7-Trichloroquinoline-3-carboxylic acid ethyl ester is also used in the synthesis of agrochemicals. Its potential biological properties, such as anti-inflammatory and antibacterial activities, make it a useful component in the development of agricultural products.
Used in Chemical Compound Production:
4,5,7-Trichloroquinoline-3-carboxylic acid ethyl ester serves as an intermediate in the production of various chemical compounds. Its unique structure allows for the creation of new compounds with potential applications in different industries.

InChI:InChI=1/C12H8Cl3NO2/c1-2-18-12(17)7-5-16-9-4-6(13)3-8(14)10(9)11(7)15/h3-5H,2H2,1H3

Upstream product

• 185011-92-1 5,7-dichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 626-43-7 3,5-Dichloroaniline 
• 93514-78-4 diethyl 2-((3,5-dichlorophenylamino)methylene)malonate 
• 93514-82-0 ethyl 4-hydroxy-5,7-dichloroquinoline-3-carboxylate 

Downstream Products

• 1207282-79-8 1-benzyl-7,9-dichloro-1H-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 1207282-76-5 2-benzyl-7,9-dichloro-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 

Relevant academic research and scientific papers

Sulfonamide-based 4-anilinoquinoline derivatives as novel dual Aurora kinase (AURKA/B) inhibitors: Synthesis, biological evaluation and in silico insights

Aurora kinases (AURKs) were identified as promising druggable targets for targeted cancer therapy. Aiming at the development of novel chemotype of dual AURKA/B inhibitors, herein we report the design and synthesis of three series of 4-anilinoquinoline derivatives bearing a sulfonamide moiety (5a-d, 9a-d and 11a-d). The percent inhibition of AURKA/B was determined for all target quinolines, then compounds showed more than 50percent inhibition on either of the enzymes, were evaluated further for their IC50 on the corresponding enzyme. In particular, compound 9d displayed potent AURKA/B inhibitory activities with IC50 of 0.93 and 0.09 μM, respectively. Also, 9d emerged as the most efficient anti-proliferative analogue in the US-NCI anticancer assay toward the NCI 60 cell lines panel, with broad spectrum activity against different cell lines from diverse cancer subpanels. Docking studies, confirmed that, the sulfonamide SO2 oxygen was involved in a hydrogen bond with Lys162 and Lys122 in AURKA and AURKB, respectively, whereas, the sulfonamide NH could catch hydrogen bond interaction with the surrounding amino acid residues Lys141, Glu260, and Asn261 in AURKA and Lys101, Glu177, and Asp234 in AURKB. Furthermore, N1 nitrogen of the quinoline scaffold formed an essential hydrogen bond with the hinge region key amino acids Ala213 and Ala173 in AURKA and AURKB, respectively.

Synthesis and biological evaluation of novel 3-(quinolin-4-ylamino)benzenesulfonamidesAQ3 as carbonic anhydrase isoforms I and II inhibitors

Carbonic anhydrases (CAs, EC 4.2.1.1) are crucial metalloenzymes that are involved in diverse bioprocesses. We report the synthesis and biological evaluation of novel series of benzenesulfonamides incorporating un/substituted ethyl quinoline-3-carboxylate moieties. The newly synthesised compounds were in vitro evaluated as inhibitors of the cytosolic human (h) isoforms hCA I and II. Both isoforms hCA I and II were inhibited by the quinolines reported here in variable degrees: hCA I was inhibited with KIs in the range of 0.966–9.091 μM, whereas hCA II in the range of 0.083–3.594 μM. The primary 7-chloro-6-flouro substituted sulphfonamide derivative 6e (KI = 0.083 μM) proved to be the most active quinoline in inhibiting hCA II, whereas, its secondary sulfonamide analog failed to inhibit the hCA II up to 10 μM, confirming the crucial role of the primary sulphfonamide group, as a zinc-binding group for CA inhibitory activity.

Synthesis and pharmacological evaluation of pyrazolo[4,3-c]quinolinones as high affinity GABAA-R ligands and potential anxiolytics

The synthesis, in vitro ligand binding study and in vivo Elevated Plus Maze test (EPM) of a series of pyrazolo[4,3-c]quinolin-3-ones (PQs) are reported. Multistep synthesis of PQs started from anilines and diethyl 2-(ethoxymethylene)malonate to give the q

Synthesis and preliminary structure-activity relationship study of 2-aryl-2H-pyrazolo[4,3-c]quinolin-3-ones as potential checkpoint kinase 1 (Chk1) inhibitors

The serine-threonine checkpoint kinase 1 (Chk1) plays a critical role in the cell cycle arrest in response to DNA damage. In the last decade, Chk1 inhibitors have emerged as a novel therapeutic strategy to potentiate the anti-tumour efficacy of cytotoxic chemotherapeutic agents. In the search for new Chk1 inhibitors, a congeneric series of 2-aryl-2 H-pyrazolo[4,3-c]quinolin-3-one (PQ) was evaluated by in-vitro and in-silico approaches for the first time. A total of 30 PQ structures were synthesised in good to excellent yields using conventional or microwave heating, highlighting that 14 of them are new chemical entities. Noteworthy, in this preliminary study two compounds 4e2 and 4h2 have shown a modest but significant reduction in the basal activity of the Chk1 kinase. Starting from these preliminary results, we have designed the second generation of analogous in this class and further studies are in progress in our laboratories.

An alternative approach toward 2-aryl-2H-pyrazolo[4,3-c]-quinolin-3-ones by a multistep synthesis

A series of 2-aryl-2H-pyrazolo[4,3-c]quinolin-3-ones derivatives 6 and 7 was conveniently prepared. A multistep synthesis was carried out starting from dichloro- and bromoanilines (1a-b) and diethyl 2-(ethoxymethylene)malonate using a slightly modified Go

New quinoline derivatives: Synthesis and evaluation for antiinflammatory and analgesic properties - Note II

The synthesis of new halogenated series of 4-anilinoquinoline-3-carboxylic acids, N-[3-carboxyquinolyl(4)]anthranilic acids and their corresponding esters is reported. These have been obtained by reacting 4-chloro-3-carbethoxyquinolines with variously substituted anilines and methyl anthranilate respectively. The synthesized compounds were tested for antiinflammatory and analgesic activities; some of them showed a good analgesic activity, sometimes higher than that of indomethacin, used as reference drug.

Pyrazolo[4,3-c]quinolines, synthesis and specific inhibition of benzodiazepine receptor binding. Note II

Two new series of 2-arylpyrazolo[4,3-c]quinolin-3-ones (6,8-difluoro- and 7,9-dichloro-derivatives) have been synthesized and tested for their ability to displace [3H]flunitrazepam from rat brain membranes. Several compounds possess comparable