3792-04-9

Usage

Uses

Used in Pharmaceutical Industry:
N-(CHLOROACETYL)-2-(TRIFLUOROMETHYL)ANILINE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, N-(CHLOROACETYL)-2-(TRIFLUOROMETHYL)ANILINE is employed as a precursor in the production of agrochemicals, potentially enhancing the effectiveness of pesticides and other agricultural chemicals.
Used in Organic Synthesis:
N-(CHLOROACETYL)-2-(TRIFLUOROMETHYL)ANILINE is utilized as a reactive intermediate in organic synthesis, allowing for the creation of a wide range of chemical compounds with diverse applications across various industries.

InChI:InChI=1/C9H7ClF3NO/c10-5-8(15)14-7-4-2-1-3-6(7)9(11,12)13/h1-4H,5H2,(H,14,15)

Upstream product

• 79-04-9 chloroacetyl chloride 
• 88-17-5 2-(trifluoromethyl)benzenamine 

Downstream Products

• 937704-78-4 C₂₂H₂₃N₂O₅F₃ 
• 138129-31-4 {4-Oxo-3-[(2-trifluoromethyl-phenylcarbamoyl)-methyl]-3,4-dihydro-phthalazin-1-yl}-acetic acid 
• 1018074-67-3 C₁₇H₁₁Cl₂F₄N₅OS 
• 867041-32-5 2-[5-(4-chloro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide 
• 867041-33-6 2-[5-(4-fluoro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide 
• 880797-78-4 2-[2,4-dioxo-5-(3-phenyl-allylidene)-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide 
• 867041-34-7 N-(4-chloro-phenyl)-2-{2,4-dioxo-3-[(2-trifluoromethyl-phenylcarbamoyl)-methyl]-thiazolidin-5-ylidene}-acetamide 
• 781656-67-5 2-{2,4-dioxo-3-[(2-trifluoromethyl-phenylcarbamoyl)-methyl]-thiazolidin-5-ylidene}-N-(4-fluoro-phenyl)-acetamide 
• 924863-99-0 2-[5-(4-dimethylamino-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide 
• 1358529-04-0 C₂₆H₁₉F₃N₄O₃ 
• 1395047-66-1 C₁₃H₁₃F₃N₂O₂S 
• 777014-22-9 2-(diethylamino)-N-(2-trifluoromethyl-phenyl)acetamide 
• 936632-71-2 1-deoxy-1-[6-(4-{[2-(trifluoromethyl)phenylcarbamoyl]methoxy}phenylamino)-9H-purin-9-yl]-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide 
• 936633-09-9 2-(4-aminophenoxy)-N-[2-(trifluoromethyl)phenyl]acetamide 

Relevant academic research and scientific papers

Design, Synthesis, Antibacterial Activity, and Mechanisms of Novel 1,3,4-Thiadiazole Derivatives Containing an Amide Moiety

To discover novel antibacterial agents, a series of novel 1,3,4-thiadiazole derivatives containing an amide moiety were designed and synthesized, and their antibacterial activities were tested. Compound 30 was designed and synthesized according to the CoMFA model. Compound 30 exhibited higher antibacterial activities against Xanthomonas oryzae pv. oryzicola and Xanthomonas oryzae pv. oryzae, with EC50 values of 2.1 and 1.8 mg/L, respectively, which were superior to those of thiodiazole copper (99.6 and 92.5 mg/L). The protective and curative activities of compound 30 against rice bacterial leaf blight were 51.3 and 46.1%, respectively, which were better than those of thiodiazole copper (37.8 and 38.5%). The protective and curative activities of compound 30 against rice bacterial leaf streak were 45.9 and 40.5%, respectively, which were better than those of thiodiazole copper (36.2 and 31.1%). In addition, the protective activity of compound 30 against rice bacterial leaf streak was related to increased activities of related defense enzymes and upregulated the differentially expressed proteins of the glycolysis/gluconeogenesis pathway.

Design, synthesis and biological evaluation of novel naturally-inspired multifunctional molecules for the management of Alzheimer's disease

In our overall goal to overcome the limitations associated with natural products for the management of Alzheimer's disease and to develop in-vivo active multifunctional cholinergic inhibitors, we embarked on the development of ferulic acid analogs. A systematic SAR study to improve upon the cholinesterase inhibition of ferulic acid with analogs that also had lower logP was carried out. Enzyme inhibition and kinetic studies identified compound 7a as a lead molecule with preferential acetylcholinesterase inhibition (AChE IC50 = 5.74 ± 0.13 μM; BChE IC50 = 14.05 ± 0.10 μM) compared to the parent molecule ferulic acid (% inhibition of AChE and BChE at 20 μM, 15.19 ± 0.59 and 19.73 ± 0.91, respectively). Molecular docking and dynamics studies revealed that 7a fits well into the active sites of AChE and BChE, forming stable and strong interactions with key residues Asp74, Trp286, and Tyr337 in AChE and with Tyr128, Trp231, Leu286, Ala328, Phe329, and Tyr341 in BChE. Compound 7a was found to be an efficacious antioxidant in a DPPH assay (IC50 = 57.35 ± 0.27 μM), and it also was able to chelate iron. Data from atomic force microscopy images demonstrated that 7a was able to modulate aggregation of amyloid β1-42. Upon oral administration, 7a exhibited promising in-vivo activity in the scopolamine-induced AD animal model and was able to improve spatial memory in cognitive deficit mice in the Y-maze model. Analog 7a could effectively reverse the increased levels of AChE and BChE in scopolamine-treated animals and exhibited potent ex-vivo antioxidant properties. These findings suggest that 7a can act as a lead molecule for the development of naturally-inspired multifunctional molecules for the management of Alzheimer's and other neurodegenerative disorders.

Antidiabetic compounds

Compounds for the treatment of hyperglycemia and/or diabetes are provided. The compounds, which inhibit the enzyme dipeptidyl peptidase (DPP-4), are based on the structure where X may be present or absent an may be OH, Ar is an aryl group; and n ranges from 0 to 5.

Design, synthesis, and SAR of novel 2-glycinamide cyclohexyl sulfonamide derivatives against botrytis cinerea

N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide (chesulfamide) is in the limelight as a novel fungicide, and has fungicidal activity against Botrytis cinerea. For exploring more novel structures, 33 new compounds were synthesized by N-alkylation and acid–amine coupling reactions with chesulfamide as the core moiety, and their structures were characterized and established by 1H-NMR, 13C-NMR, MS, and elemental analysis. The structure of (1R,2S)-2-(2-(N-(4-chloro-2-trifluoromethylphenyl)sulfamoyl)-cyclohexylamino)-N-(2-trifluoromethylphenyl) acetamide (II-19) was defined by X-ray single crystal diffraction. The in vivo and in vitro fungicidal activities against B. cinerea were evaluated. The bioassay results of mycelial growth demonstrated that most compounds exhibited excellent inhibitory activity against B. cinerea at 50 μg mL?1, and 7 compounds showed lower EC50 values than boscalid (EC50 = 4.46 μg mL?1) against B. cinerea (CY-09). In cucumber pot experiment, the inhibitory rates of four compounds (II-4, II-5, II-12, and II-13) against B. cinerea were 90.48, 93.45, 92.86, and 91.07, which were better than cyprodinil (88.69%), the best performing of all controls. In tomato pot experiment, the control efficacy of two analogs (II-8 and II-15) were 87.98 and 87.97% at 200 μg mL?1, which were significantly higher than boscalid (78.10%). Most compounds have an excellent fungicidal effect on B. cinerea, with potential as a lead compound for developing new pesticides.

Synthesis and biological evaluation of N-(substituted phenyl)-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)acetamides as antimicrobial, antidepressant, and anticonvulsant agents

A new series of N-Aryl-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)acetamides were synthesized by condensation of tricyclic compound 2,5-dihydro-3H-[1,2,4]triazino[5,6-b]indole-3-thione with chloro N-phenylacetamides. The tricyclic compound was obtaine

Development of Small-Molecule Cryptochrome Stabilizer Derivatives as Modulators of the Circadian Clock

Small-molecule probes have been playing prominent roles in furthering our understanding of the molecular underpinnings of the circadian clock. We previously discovered a carbazole derivative, KL001 (N-(3-(9H-carbazol-9-yl)-2-hydroxypropyl)-N-(furan-2-ylme

Synthesis and cytotoxic evaluation of some new phthalazinylpiperazine derivatives

A new series of 1,4-disubstituted phthalazinylpiperazine derivatives 7a-f, 12a-f and 20a-f were designed and synthesized in order to develop potent and selective antitumor agents. The target compounds were screened for their cytotoxic activities against A549, HT-29 and MDA-MB-231 cancer cell lines in vitro. Among them, compounds 7a-f exhibited excellent selectivity for MDA-MB-231 with IC50 values ranging from 0.013 μM to 0.079 μM. The most promising compound, 7e (IC50 = 2.19 μM, 2.19 μM, 0.013 μM), was 9.3, 10, and 4.9 × 103 times more active than vatalanib (IC50 = 20.27 μM, 21.96 μM, 63.90 μM), respectively. A new series of 1,4-disubstituted phthalazinylpiperazine derivatives 7a-f, 12a-f and 20a-f were designed and synthesized, and their cytotoxic activities against A549, HT-29 and MDA-MB-231 cancer cell lines in vitro were compared to that of vatalanib.

Hydrazones derived from thiooxamohydrazides and 3-formyl-4-hydroxycoumarin: Synthesis, structures, and fragmentation

Novel hydrazones were obtained from thiooxamohydrazides and 3-3-formyl-4-hydroxycoumarin. According to data from NMR spectroscopy and X-ray diffraction, the coumarin fragment in the compounds obtained exists as 4-hydroxycoumarin or chromane-2,4-dione. When dissolved in dimethyl sulfoxide, these hydrazones undergo fragmentation into derivatives of 1,3,4-thiadiazole and 4-hydroxycoumarin.

Design principles and theory of paramagnetic fluorine-labelled lanthanide complexes as probes for19F magnetic resonance: a proof-of-concept study

The synthesis and spectroscopic properties of a series of CF 3-labelled lanthanide(III) complexes (Ln = Gd, Tb, Dy, Ho, Er, Tm) with amidesubstituted ligands based on 1,4,7,10tetraazacyclododecane are described. The theoretical contributions of

Synthesis and biological evaluation of 1,4-diazepane derivatives as T-type calcium channel blockers

We have synthesized and biologically evaluated 1,4-diazepane derivatives as T-type calcium channel blockers. In this study, we discovered compound 4s, a potential T-type calcium channel blocker with good selectivity over hERG and N-type calcium channels. In addition, it exhibited favorable pharmacokinetic characteristics for further investigation of T-type calcium channel related diseases.