574-92-5

Usage

Uses

Used in Chemical Synthesis:
4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID is used as a key intermediate in the synthesis of various complex organic molecules, particularly in the preparation of (4-hydroxy-7-trifluoromethylquinolin-3-yl)formaldehyde. 4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID serves as a building block for the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID is used as a starting material for the development of novel drugs with potential therapeutic applications. Its unique chemical structure allows for the creation of new molecules with specific biological activities, targeting various diseases and medical conditions.
Used in Research and Development:
4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID is also utilized in research and development laboratories for the study of its chemical properties, reactivity, and potential applications in various fields. Researchers use 4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID to explore new reaction pathways, develop innovative synthetic methods, and gain insights into the structure-activity relationships of related molecules.
Used in Material Science:
In the field of material science, 4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID may find applications in the development of new materials with specific properties, such as optical, electronic, or magnetic functionalities. Its unique chemical structure can be exploited to design and synthesize novel materials with tailored characteristics for various applications, including sensors, displays, and energy storage devices.

InChI:InChI=1/C11H6F3NO3/c12-11(13,14)5-1-2-6-8(3-5)15-4-7(9(6)16)10(17)18/h1-4H,(H,15,16)(H,17,18)

Upstream product

• 391-02-6 4-hydroxy-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester 
• 98-16-8 3-trifluoromethylaniline 
• 141-97-9 ethyl acetoacetate 
• 370-35-4 diethyl 2-({[3-(trifluoromethyl)phenyl]amino}methylidene)propanedioate 

Downstream Products

• 322-97-4 7-trifluoromethyl-quinolin-4-ol 
• 59197-90-9 4-Hydroxy-7-trifluormethyl-3-chinolincarbonsaeurechlorid 
• 1471178-23-0 1-(4-cyanobenzyl)-4-oxo-8-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1471178-17-2 1-(4-cyanobenzyl)-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1471178-21-8 1-(2,4-dichlorobenzyl)-4-oxo-8-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1471178-15-0 1-(2,4-dichlorobenzyl)-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 346-55-4 4-chloro-7-trifluoromethyl quinoline 

Relevant academic research and scientific papers

Reactivity and Anticancer Assessment of 4-Hydroxyquinoline Derivatives

Abstract: Ethyl 4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylate (1) exhibits a moderate cytotoxic activity against the MCF-7 mammary gland cancer cell line and HePG2 hepatocellular carcinoma cell line and a weak activity against the HCT-116 human colorectal carcinoma cell line. In order to enhance the cytotoxic activity of this compound, it was modified by changing the side-chain substituent and/or forming a new heterocyclic ring fused to the pyridine ring. Heating compound 1 with chloroacetyl chloride gave a mixture of two isomeric O-acylation products ethyl 4-(2-chloroacetoxy)-7-(trifluoromethyl)-quinoline-3-carboxylate and 3-chloro-8-(trifluoromethyl)-2H-pyrano[3,2-c]quinoline-2,4(3H)-dione, whereas the reaction with acetyl chloride in NaOH formed an N-acylation product 1-acetyl-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid. The reactions of compound 1 with urea, thiourea, hydrazine hydrate, hydroxylamine, o-phenylenediamine, phenyl isothiocyanate, and ethyl acetoacetate yielded the corresponding condensation products 1-[4-oxo-7-(trifluoromethyl)-3,4-dihydroquinoline-3-carbonyl)]urea, 1-[4-oxo-7-(trifluoromethyl)-3,4-dihydroquinoline-3-carbonyl)]thiourea, 7-(trifluoromethyl)-1,2-dihydropyrazolo[4,3-c]quinolin-3-one, 7-(trifluoromethyl)isoxazolo[4,5-c]quinolin-3(2H)-one, 3-(trifluoromethyl)-13H-benzo[2,3][1,4]diazepino[6,5-c]quinolin-7-ol, 3-phenyl-2-thioxo-8-(trifluoromethyl)-2,3-dihydro-4H-[1,3]oxazino[5,6-c]quinolin-4-one and ethyl 8-(trifluoromethyl)-2-methyl-4-oxo-4H-pyrano[3,2-c]quinolone 3-carboxylate, respectively. The structures of the synthesized compounds were confirmed by elemental analysis and spectral data.

Design and regioselective synthesis of trifluoromethylquinolone derivatives as potent antimicrobial agents

Three series of new trifluoromethyl substituted quinolone derivatives were synthesized (4a-f, 6a-f and 8a-f) from corresponding substituted anilines by multi-step reactions. The regioselective alkylation with different alkyl halides were carried out by approaching two different routes to get the final products in good yield. Newly synthesized compounds were characterized by spectral study and also by C, H, N analyses. Three dimensional structure of 2b and 4b were also confirmed by single crystal X-ray studies. The final compounds (4a-f, 6a-f and 8a-f) were screened for their in-vitro antibacterial and antifungal activity by well plate method (zone of inhibition). The results revealed that, compounds 4a, 6b, 6c and 8e showed significant antibacterial activity as compared to the standard drug Ciprofloxacin. The compound 8a was found to be a potent antifungal agent.

Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof

Thiazolo-, oxazolo- and selenazolo[4,5-c]quinolin-4-amines and analogs thereof are described including methods of manufacture and the use of novel intermediates. The compounds are immunomodulators and induce cytokine biosynthesis, including interferon and/or tumor biosynthesis, necrosis factor, and inhibit the T-helper-type 2 immune response. The compounds are further useful in the treatment of viral and neoplastic diseases.

Structure-activity relationships for antiplasmodial activity among 7- substituted 4-aminoquinolines

Aminoquinolines (AQs) with diaminoalkane side chains (-HNRNEt2) shorter or longer than the isopentyl side chain [-HNCHMe(CH2)3NEt2] of chloroquine are active against both chloroquine-susceptible and -resistant Plasmodium falciparum. (De, D.; et al. Am. J. Trop. Med. Hyg. 1996, 55, 579-583). In the studies reported here, we examined structure-activity relationships (SARs) among AQs with different N,N-diethyldiaminoalkane side chains and different substituents at the 7-position occupied by Cl in chloroquine. 7-Iodo- and 7- bromo-AQs with diaminoalkane side chains [-HN(CH2)2NEt2, -HN(CH2)3NEt2, or -HNCHMeCH2NEt2] were as active as the corresponding 7-chloro-AQs against both chloroquine-susceptible and -resistant P. falciparum (IC50s of 3-12 nM). In contrast, with one exception, 7-fluoro-AQs and 7-trifluoromethyl-AQs were less active against chloroquine-susceptible P. falciparum (IC50s of 15-50 nM) and substantially less active against chloroquine-resistant P. falciparum (IC50s of 18-500 nM). Furthermore, most 7-OMe-AQs were inactive against both chloroquine-susceptible (IC50s of 17-150 nM) and -resistant P. falciparum (IC50s of 90-3000 nM).