1743-86-8

Usage

Uses

Used in Research Applications:
2-(TRIFLUOROMETHYL)PHENYL ISOTHIOCYANATE is used as a specialty chemical for research purposes, particularly in the field of organic synthesis. Its unique structure and properties make it a valuable compound for studying chemical reactions and developing new synthetic pathways.
Used in Organic Synthesis:
In the field of organic chemistry, 2-(TRIFLUOROMETHYL)PHENYL ISOTHIOCYANATE is used as a key intermediate or reagent in the synthesis of various complex molecules. Its presence of a trifluoromethyl group and an isothiocyanate group allows for a wide range of reactions, making it a versatile building block for the creation of new compounds.
Used in Pharmaceutical Industry:
2-(TRIFLUOROMETHYL)PHENYL ISOTHIOCYANATE is used as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its unique chemical properties can be exploited to develop new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
2-(TRIFLUOROMETHYL)PHENYL ISOTHIOCYANATE is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its chemical structure can be modified to create new active ingredients with improved efficacy and selectivity.
Used in Material Science:
2-(TRIFLUOROMETHYL)PHENYL ISOTHIOCYANATE is used in the development of new materials with specific properties, such as high thermal stability, chemical resistance, or unique optical characteristics. Its incorporation into polymers or other materials can lead to the creation of advanced materials for various applications.

InChI:1S/C8H4F3NS/c9-8(10,11)6-3-1-2-4-7(6)12-5-13/h1-4H

Upstream product

• 1736-71-6 2-trifluoromethylphenyl thiourea 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 75-15-0 carbon disulfide 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 463-71-8 thiophosgene 

Downstream Products

• 1744-41-8 1-Guanyl-4-<2-trifluormethyl-phenyl>-thiosemicarbazid 
• 132418-41-8 6-(2-chlorophenyl)-7,10-dihydro-1-methyl-N-(2-trifluoromethylphenyl)-4H-pyrido[4',3';4,5]thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-9(8H)-carbothioamide 
• 186371-11-9 3-hydroxy-5-[(5-nitrothiazol-2-yl)mercapto]-4-[2-(trifluoromethyl) phenyl]-1,2,4-triazole 
• 1056619-28-3 2-(2-trifluoromethylphenylamino)-1H-benzoimidazole-5-carboxylic acid 
• 303056-17-9 C₁₀H₆F₃NOS₂ 
• 611212-85-2 N-methyl[4-(2-{[2-(trifluoromethyl)phenyl]amino}-benzimidazol-5-yloxy)(2-pyridyl)]-carboxamide 
• 611214-05-2 N-methyl[4-(1-methyl-2-{[2-(trifluoromethyl)phenyl]amino}benzimidazol-5-yloxy)(2-pyridyl)]-carboxamide 
• 848252-40-4 N-(3-amino-4-thienyl)-N'-(2-trifluorophenyl)thiourea 
• 497077-97-1 2-(4-{[(2-trifluoromethylphenyl)amino]carbonothioyl}-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid 
• 1346176-67-7 4-(2-trifluoromethylphenyl)-1-(4-methylthiadiazol-5-yl)carbonylthiosemicarbazide 

Relevant academic research and scientific papers

4H-PYRROLO[3,2-C]PYRIDIN-4-ONE DERIVATIVES

Compounds of formula (I) for use in the treatment or prophylaxis of a disease, which is a hyperproliferative disease and/or a disorder responsive to induction of cell death, selected from a haematological tumour, a solid tumour and/or metastases thereof, said tumour harbouring a mutant EGFR with exon 19 or 21 mutations, and their use as pharmaceuticals.

The novel copper(I) π,σ-complexes with 1-(aryl)-5-(allylthio)-1H-tetrazoles: Synthesis, structure characterization, DFT-calculation and third-order nonlinear optics

The present work is directed toward preparation, structure and optical property characterization of tetrazole-containing Cu(I) compounds. By means of the alternating-current electrochemical technique copper(I) π,σ-compounds with 1-(4-methylphenyl)- (Matht), 1-(3-chloro-4-methylphenyl)- (Chmatht) and 1-[2-(trifluoromethyl)phenyl]- (Tfmatht) 5-(allylthio)-1H-tetrazoles were obtained in a single crystal form and structurally characterized by X-ray diffraction and Raman spectroscopy. Matht and Chmatht ligands, being attached to the Cu(I) through S-allylic C = C-bond and two tetrazole N-atoms, form stable centrosymmetric dimers [Cu2(Matht)2(H2O)2](BF4)2 and [Cu2(Chmatht)2(СlO4)2]. The presence of an electron acceptor trifluoromethyl group promotes formation of the monomeric [Cu(Tfmatht)2]BF4 and [Cu(Tfmatht)(NH2SO3)(MeOH)] compounds. The compounds were investigated by means of Raman spectroscopy, third-order nonlinear optics and DFT calculations.

4H-PYRROLO[3,2-C]PYRIDIN-4-ONE DERIVATIVES

Compounds of formula (I) processes for their production and their use as pharmaceuticals.

Differentiating Antiproliferative and Chemopreventive Modes of Activity for Electron-Deficient Aryl Isothiocyanates against Human MCF-7 Cells

The consumption of Brassica vegetables provides beneficial effects through organic isothiocyanates (ITCs), products of the enzymatic hydrolysis of glucosinolate secondary metabolites. The ITC l-sulforaphane (l-SFN) is the principle agent in broccoli that demonstrates several modes of anticancer action. While the anticancer properties of ITCs like l-SFN have been extensively studied and l-SFN has been the subject of multiple human clinical trials, the scope of this work has largely been limited to those derivatives found in nature. Previous studies have demonstrated that structural changes in an ITC can lead to marked differences in a compound's potency to 1) inhibit the growth of cancer cells, and 2) alter cellular transcriptional profiles. This study describes the preparation of a library of non-natural aryl ITCs and the development of a bifurcated screening approach to evaluate the dose- and time-dependence on antiproliferative and chemopreventive properties against human MCF-7 breast cancer cells. Antiproliferative effects were evaluated using a commercial MTS cell viability assay. Chemopreventive properties were evaluated using an antioxidant response element (ARE)-promoted luciferase reporter assay. The results of this study have led to the identification of 1) several key structure–activity relationships and 2) lead ITCs for continued development.

Inhibitors of the Diadenosine Tetraphosphate Phosphorylase Rv2613c of Mycobacterium tuberculosis

The intracellular concentration of diadenosine tetraphospate (Ap4A) increases upon exposure to stress conditions. Despite being discovered over 50 years ago, the cellular functions of Ap4A are still enigmatic. If and how the varied Ap4A is a signal and involved in the signaling pathways leading to an appropriate cellular response remain to be discovered. Because the turnover of Ap4A by Ap4A cleaving enzymes is rapid, small molecule inhibitors for these enzymes would provide tools for the more detailed study of the role of Ap4A. Here, we describe the development of a high-throughput screening assay based on a fluorogenic Ap4A substrate for the identification and optimization of small molecule inhibitors for Ap4A cleaving enzymes. As proof-of-concept we screened a library of over 42, 000 compounds toward their inhibitory activity against the Ap4A phosphorylase (Rv2613c) of Mycobacterium tuberculosis (Mtb). A sulfanylacrylonitril derivative with an IC50 of 260 ± 50 nM in vitro was identified. Multiple derivatives were synthesized to further optimize their properties with respect to their in vitro IC50 values and their cytotoxicity against human cells (HeLa). In addition, we selected two hits to study their antimycobacterial activity against virulent Mtb to show that they might be candidates for further development of antimycobacterial agents against multidrug-resistant Mtb.

N,N'-bis-substituted aryl thiourea derivatives and synthetic method and application thereof

The invention discloses N,N'-bis-substituted aryl thiourea derivatives which are a series of compounds simultaneously containing various substituted aromatic ring structures and asymmetric substituted thiourea structures and are all novel structural compounds which are not reported in the literature. The biological activity test analysis of all the target compounds includes determination of DPPH antioxidant activity and antiviral activity. Results indicate that, in general, the designed and synthesized compounds are novel in structures and have the antioxidant activity and the antiviral activity revealed for the first time. In addition, the unknown biological activity is not fully elucidated, and thus the compounds are expected to provide a certain material basis for further research and development of new drugs.

Design and synthesis of novel bicalutamide and enzalutamide derivatives as antiproliferative agents for the treatment of prostate cancer

Prostate cancer (PC) is one of the major causes of male death worldwide and the development of new and more potent anti-PC compounds is a constant requirement. Among the current treatments, (R)-bicalutamide and enzalutamide are non-steroidal androgen receptor antagonist drugs approved also in the case of castration-resistant forms. Both these drugs present a moderate antiproliferative activity and their use is limited due to the development of resistant mutants of their biological target. Insertion of fluorinated and perfluorinated groups in biologically active compounds is a current trend in medicinal chemistry, applied to improve their efficacy and stability profiles. As a means to obtain such effects, different modifications with perfluoro groups were rationally designed on the bicalutamide and enzalutamide structures, leading to the synthesis of a series of new antiproliferative compounds. Several new analogues displayed improved in vitro activity towards four different prostate cancer cell lines, while maintaining full AR antagonism and therefore representing promising leads for further development. Furthermore, a series of molecular modelling studies were performed on the AR antagonist conformation, providing useful insights on potential protein-ligand interactions.

Double three bromo 1,3-di-pyridine salt-based propane and its preparation method, method of use, recovery method and application

The invention discloses a double tribromo 1,3-bipyridine onium salt dimethylmethane, and a preparation method, an application method, a recovery method and application thereof. The preparation method comprises the following steps: dissolving 1,3-bipyridine onium salt dimethylmethane by using water, and then adding potassium bromide; adding potassium peroxymonosulfate sulfate compound brine solution to prepare a clear solution after dissolving potassium bromide, and then stirring and reacting at -10 to 0 DEG C until solid is separated out; separating out solid, so as to obtain the double tribromo 1,3-bipyridine onium salt dimethylmethane. The product can be used for preparing isothiocyanate, aromatic thiourea or acetanilide. The preparation method disclosed by the invention is mild in condition, and simple to operate the reaction process, and raw materials are easily available. The double tribromo 1,3-bipyridine onium salt dimethylmethane not only can be used as a brominating reagent, but also can be used as organic synthesis intermediates, meanwhile, the reaction efficiency is improved, and the double tribromo 1,3-bipyridine onium salt dimethylmethane is convenient to recover and can be recycled.

Pyrazolopyrimidines: Potent Inhibitors Targeting the Capsid of Rhino- and Enteroviruses

There are currently no drugs available for the treatment of enterovirus (EV)-induced acute and chronic diseases such as the common cold, meningitis, encephalitis, pneumonia, and myocarditis with or without consecutive dilated cardiomyopathy. Here, we report the discovery and characterization of pyrazolopyrimidines, a well-tolerated and potent class of novel EV inhibitors. The compounds inhibit the replication of a broad spectrum of EV in vitro with IC50 values between 0.04 and 0.64 μM for viruses resistant to pleconaril, a known capsid-binding inhibitor, without affecting cytochrome P450 enzyme activity. Using virological and genetics methods, the viral capsid was identified as the target of the most promising, orally bioavailable compound 3-(4-trifluoromethylphenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine (OBR-5-340). Its prophylactic as well as therapeutic application was proved for coxsackievirus B3-induced chronic myocarditis in mice. The favorable pharmacokinetic, toxicological, and pharmacodynamics profile in mice renders OBR-5-340 a highly promising drug candidate, and the regulatory nonclinical program is ongoing. Curing the common cold! A cluster of pyrazolopyrimidines with potent broad-spectrum activity against enteroviruses was discovered. Extensive structure-property relationship analyses led to the identification of 3-(4-trifluoromethyl-phenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine, shown to be a blocker of the viral capsid protein, as a lead compound for drug development with favorable physicochemical, pharmacokinetic, and toxicological properties.

Diversity-orientated synthesis of 3,5-bis(arylamino)pyrazoles

The synthesis of differentially-substituted 3,5-bis(arylamino)pyrazoles has not yet been documented. During our investigation, we managed to develop a novel, entirely combinatorial synthesis of 3,5-bis(arylamino)pyrazoles relying on a simple one-pot two-step operation.