83842-55-1

Basic information

• Product Name: 2-Trifluoromethyl-1H-quinolin-4-one
• Synonyms: 2-Trifluoromethyl-1H-quinolin-4-one;2-(trifluoroMethyl)-1,4-dihydroquinolin-4-one;2-(trifluoromethyl)-4(1H)-Quinolinone
• CAS NO: 83842-55-1
• Molecular Formula: C10H6F3NO
• Molecular Weight: 213.1559496
• Mol File: 83842-55-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Trifluoromethyl-1H-quinolin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Trifluoromethyl-1H-quinolin-4-one(83842-55-1)
• EPA Substance Registry System: 2-Trifluoromethyl-1H-quinolin-4-one(83842-55-1)

Safety Data

• Hazardous Substances Data: 83842-55-1(Hazardous Substances Data)

Usage

General Description

2-Trifluoromethyl-1H-quinolin-4-one is a chemical compound belonging to the quinoline class. It is also known as CF3-quinolin-4-one or 2-trifluoromethylquinolin-4(1H)-one. 2-Trifluoromethyl-1H-quinolin-4-one has a molecular formula of C10H6F3NO and a molecular weight of 207.15 g/mol. It is a yellow solid with a melting point of 89-91°C. 2-Trifluoromethyl-1H-quinolin-4-one is used as a building block in the synthesis of pharmaceutical and agrochemical compounds. It has the potential to exhibit biological activity and may have applications in drug discovery and development.

Upstream product

• 6141-26-0 2-Trifluoroacetylaminoacetophenone 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 551-93-9 2-aminoacetophenone 
• 62-53-3 aniline 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 535993-23-8 3,3-dihydroxy-1-(2-trifluoroacetamidophenyl)-4,4,4-trifluorobutan-1-one 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 587886-11-1 4-bromo-2-trifluoromethyl-3-quinolinecarboxylic acid 
• 587886-19-9 4-bromo-2-trifluoromethyl-3-quinolinecarboxylic acid methyl ester 
• 587886-26-8 2-trifluoromethyl-3-quinolinecarboxylic acid 
• 18706-39-3 2-(trifluoromethyl)quinoline-4-carboxylic acid 
• 18706-25-7 4-bromo-2-(trifluoromethyl)quinoline 

Relevant articles and documents

Quinoline and ferrocene conjugates: Synthesis, computational study and biological evaluations

Novel O-alkylated quinoline and N-alkylated 4-quinolone derivatives attached to the ferrocene moiety through 4,1- (7a–d, 8a–d and 12a–d) and 1,4-disubstituted (9a, 9b, 10a and 10b) 1,2,3-triazole moiety were synthesized. The observed regioselectivity of O- vs. N-alkylation was explored by the use of NMR and computational techniques. Among the N-alkylated derivatives, the quinolone-ferrocene conjugate 9a displayed marked activities against chronic myeloid leukemia in blast crisis (K562) and Burkitt lymphoma (Raji). The 6-chloroquinolone-ferrocene conjugate 12c, with selective inhibitory activity on Raji cells and no cytostatic effect on normal MDCK1 cells was highlighted as the most promising anticancer organometallic complex in a group of O-alkylated quinolines.

Design and synthesis of ibuprofen-quinoline conjugates as potential anti-inflammatory and analgesic drug candidates

A new set of ibuprofen-quinoline conjugates comprising quinolinyl heterocycle and ibuprofen moieties linked by an alkyl chain were synthesized in good yields utilizing an optimized reaction procedure in a molecular hybridization approach to overcome the drawbacks of the current non-steroidal anti-inflammatory drugs. The synthesized conjugates were screened for their anti-inflammatory, and ulcerogenic properties. Several conjugates were found to have significant anti-inflammatory properties in the carrageenan-induced rat paw edema test without showing any ulcerogenic liability. In addition, most conjugates showed promising peripheral analgesic activity in the acetic acid-induced writhing test as well as central analgesic properties in the in vivo hot plate test. The most promising conjugates were the unsubstituted and 6-substituted fluoro- and chloro-derivatives of 2-(trifluoromethyl)quinoline linked to ibuprofen by a propyl chain. Their anti-inflammatory activity was evaluated against LPS-stimulated inflammatory reactions in RAW264.7 mouse macrophages. In this regard, it was found that most of the conjugates were able to significantly reduce the release and production of nitric oxide in the LPS-stimulated macrophages. The secretion and expression of the pro-inflammatory cytokines IL-6, TNF-α, and inducible nitric oxide synthase (iNOS) were also significantly suppressed.

New trifluoromethyl quinolone derivatives: Synthesis and investigation of antimicrobial properties

A series of quinolone derivatives, containing different heterocyclic amines were prepared. Synthesized compounds were evaluated for their in vitro antimicrobial activities against two Gram-positive bacteria, three Gram-negative bacteria as well as four fungi. All the derivatives showed good activity towards Gram-positive bacteria and less activity towards Gram-negative bacteria. They also showed moderate to comparable activity against Aspergillus niger and Candida albicans and low to moderate antifungal activity against Aspergillus fumigatus and Aspergillus flavus.