23779-97-7

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-8-(trifluoromethyl)quinoline is used as a reagent for the potent CRTh2 (DP2) receptor antagonists discovery. These antagonists are crucial in the treatment of asthma, allergic rhinitis, and other inflammatory diseases. The compound plays a vital role in the development of new therapeutic agents that can effectively manage these conditions by targeting the specific receptors involved in the inflammatory response.

InChI:InChI=1/C5H8F3NO2/c6-5(7,8)2-1-3(9)4(10)11/h3H,1-2,9H2,(H,10,11)

Synthetic route

8-(trifluoromethyl)quinoline-4(1H)-one (93919-57-4, 23779-96-6) → 4-chloro-8-(trifluoromethyl)quinoline (23779-97-7)

Conditions	Yield
With trichlorophosphate at 100℃; for 0.25h; Inert atmosphere;	95%
Stage #1: 8-(trifluoromethyl)quinoline-4(1H)-one With trichlorophosphate at 110℃; for 2h; Stage #2: With sodium hydroxide for 18h;	92%

Upstream product

• 23779-96-6 4-hydroxy-8-trifluoromethylquinoline 
• 71002-49-8 β-(o-trifluoromethylanilino)-propanoic acid 
• 93919-57-4 8-(trifluoromethyl)quinoline-4(1H)-one 
• 34067-83-9 N-(phenyl)pyrazine-2-carboxamide 
• 24691-94-9 N-phenyl-3-methyl-2-pyridinecarboxamide 
• 1575754-64-1 N-phenylisoquinoline-3-carboxamide 
• 72787-99-6 N-phenyl-isoquinoline-1-carboxamide 
• 314055-37-3 N-(2-(trifluoromethyl)phenyl)pyrazine-2-carboxamide 
• 31601-87-3 3-carbethoxy-8-trifluoromethyl-4-quinolone 
• 31601-88-4 3-carboxy-8-trifluoromethyl-4-quinolone 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 10354-53-7 N-phenylpicolinamide 
• 450383-19-4 2,2-dimethyl-5-({[2-(trifluoromethyl)phenyl]amino}methylidene)-1,3-dioxane-4,6-dione 

Downstream Products

• 23779-99-9 floctafenine 
• 61149-27-7 dimethylphosphinylmethyl N-(8-trifluoromethyl-4-quinoyl)-anthranilate 
• 57369-92-3 4-hydrazineyl-8-(trifluoromethyl)quinoline 

Relevant academic research and scientific papers

Design, synthesis and characterization of new 1,2,3-triazolyl pyrazole derivatives as potential antimicrobial agents: Via a Vilsmeier-Haack reaction approach

The synthesis of a new series of 3-{5-methyl-1-[2-methyl-3-(trifluoromethyl) phenyl/substituted phenyl]-1H-1,2,3-triazol-4-yl}-1-(aryl)-1H-pyrazole-4-carbaldehyde compounds (5a-n) was carried out via a Vilsmeier-Haack formylation of 4-{(1E)-1-[2-(aryl) hydrazinylidene]ethyl}-5-methyl-1-[2-methyl-3-(trifluoromethyl)phenyl/substituted phenyl]-1H-1,2,3-triazole (4a-n) with a phosphorous oxychloride and DMF mixture. The newly synthesized compounds were characterized using IR, 1H NMR, 13C NMR, mass spectral data and elemental analysis. The newly synthesized compounds were screened for their in vitro anti-bacterial, anti-fungal and anti-oxidant activities. Some of the synthesized compounds displayed a broad spectrum of antimicrobial activities and moderate to good anti-oxidant activities. The anti-bacterial results were further supported by in silico molecular docking studies of these compounds for the inhibition of E. coli MurB enzyme (PDB code: 2MBR) and showed a minimum binding energy and good affinity towards the active pocket comparable with the standard drug Ciproflaxin. Thus, they may be considered as good inhibitors of the E. coli MurB enzyme (PDB code: 2MBR).

Unsymmetrical bisquinolines with high potency against P. falciparum Malaria

Quinoline-based scaffolds have been the mainstay of antimalarial drugs, including many artemisinin combination therapies (ACTs), over the history ofmoderndrugdevelopment. Althoughmuch progress has beenmade in the search for novel antimalarial scaffolds, itmay be that quinolineswill remain useful, especially if very potent compounds fromthis class are discovered. We report here the results of a structure-activity relationship(SAR) study assessingpotentialunsymmetrical bisquinoline antiplasmodial drug candidates using in vitro activity against intact parasites in cell culture. Many unsymmetrical bisquinolineswere found to be highly potent against both chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum parasites. Further work to develop such compounds could focus on minimizing toxicities in order to find suitable candidates for clinical evaluation.

Coordinating Activation Strategy-Induced Selective C?H Trifluoromethylation of Anilines

A simple protocol for the synthesis of 2-(trifluoromethyl)aniline derivatives through a coordinating activation strategy was developed. The reaction showed good reactivity and gave the target products in moderate to good yields. Pleasingly, the directing group could be recovered in excellent yield. Furthermore, this strategy allowed efficient access to the synthesis of floctafenine. A single-electron-transfer mechanism was proposed to be responsible for this trifluoromethylation reaction.

Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities

A simple two-step synthesis method was used to make 51 B-ring-substituted 4-hydroxyquinolines allowing analysis of the effect of ring substitutions on inhibition of growth of chloroquine sensitive and resistant strains of Plasmodium falciparum, the dominant cause of malaria morbidity. Substituted quinoline rings other than the 7-chloroquinoline ring found in chloroquine were found to have significant activity against the drug-resistant strain of P. falciparum W2.

Process for the preparation of 4-chloroquinolines

Novel process for the preparation of 4-chloroquinolines of the formula STR1 wherein X is in the 5,6,7 or 8-position and is selected from the group consisting of hydrogen, methyl, halogen, CF3 --, CF3 O-- and CF3 S-- by reacting a compound of the formula STR2 or a functional derivative thereof with a chlorination agent in the presence of an oxidation agent and to a novel intermediate.