1736-70-5

Basic information

• Product Name: 3-(TRIFLUOROMETHYL)PHENYLTHIOUREA
• Synonyms: 1-[3-(TRIFLUOROMETHYL)PHENYL]-2-THIOUREA;3-(TRIFLUOROMETHYL)PHENYLTHIOUREA;alpha,alpha,alpha-Trifluoro-m-tolylthiourea;à,à,à-trifluoro-m-tolylthiourea;1-[3-(Trifluoromethyl)phenyl]-2-thiourea 97%;1-[3-(Trifluoromethyl)phenyl]-2-thiourea97%;N-[3-(TRIFLUOROMETHYL)PHENYL]THIOUREA;3-METHYL-5-(CHLOROMETHYL)PYRIDINE HCL
• CAS NO: 1736-70-5
• Molecular Formula: C₈H₇F₃N₂S
• Molecular Weight: 220.21
• Product Categories: Heterocycles
• Mol File: 1736-70-5.mol

Chemical Properties

• Melting Point: 104-108 °C(lit.)
• Boiling Point: 264.6 °C at 760 mmHg
• Flash Point: 113.8 °C
• Appearance: /
• Density: 1.457 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.46±0.70(Predicted)
• BRN: 2695477
• CAS DataBase Reference: 3-(TRIFLUOROMETHYL)PHENYLTHIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(TRIFLUOROMETHYL)PHENYLTHIOUREA(1736-70-5)
• EPA Substance Registry System: 3-(TRIFLUOROMETHYL)PHENYLTHIOUREA(1736-70-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/22-36-43
• Safety Statements: 26-37/39
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1736-70-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-(TRIFLUOROMETHYL)PHENYLTHIOUREA is used as a key intermediate in the synthesis of pharmaceuticals for its ability to improve the bioactivity and metabolic stability of the resulting compounds. The trifluoromethyl group is known to enhance the lipophilicity and membrane permeability of drugs, which can lead to better pharmacokinetic properties and therapeutic effects.
Used in Agrochemical Development:
In the agrochemical industry, 3-(TRIFLUOROMETHYL)PHENYLTHIOUREA is utilized as a building block in the creation of new agrochemicals. The introduction of the trifluoromethyl group can enhance the pesticidal activity and selectivity of these compounds, making them more effective in protecting crops against pests and diseases.
Used in Biochemical Research:
3-(TRIFLUOROMETHYL)PHENYLTHIOUREA is employed as a reagent in biochemical research to study its potential antiviral and antitumor properties. Its unique structure allows researchers to investigate its interactions with biological targets and evaluate its efficacy in inhibiting viral replication or tumor growth, which could lead to the development of new therapeutic agents.
Used in Organic Synthesis:
As a versatile organic synthesis reagent, 3-(TRIFLUOROMETHYL)PHENYLTHIOUREA is used to introduce the trifluoromethyl group into a variety of organic molecules. This modification can significantly alter the physical, chemical, and biological properties of these molecules, making them suitable for various applications in materials science, medicinal chemistry, and other fields.

InChI:InChI=1/C8H6F3N2S/c9-8(10,11)6-2-1-3-7(4-6)13-5-14-12/h1-4H,12H2

Upstream product

• 98-16-8 3-trifluoromethylaniline 
• 1840-19-3 1-isothiocyanato-3-trifluoromethyl-benzene 
• 540-72-7 sodium thiocyanide 
• 532-55-8 Benzoyl isothiocyanate 
• 89069-94-3 N-{[3-(trifluoromethyl)phenyl]carbamothioyl}benzamide 

Downstream Products

• 88352-42-5 N-(3-Trifluoromethylphenyl)-S-methyl isothiourea 
• 65069-76-3 2-Methyl-1-(3-trifluoromethyl-phenyl)-isothiourea; hydriodide 
• 74466-99-2 [1,2,4]Thiadiazol-5-yl-(3-trifluoromethyl-phenyl)-amine 
• 867315-06-8 4-(chloromethyl)-N-[3-(trifluoromethyl)phenyl]-1,3-thiazolyl-2-amine 
• 792902-47-7 2-(3-trifluoromethylphenylamino)4-(4-chlorophenyl)thiazole 
• 898522-67-3 2-(3-trifluoromethylphenylamino)-4-(4-bromophenyl)thiazole 
• 71173-38-1 3-(trifluoromethyl)phenylcyanamide 
• 1269487-77-5 (4S)-4-(N-benzyloxycarbonyl-2-aminoethyl)-2-[(3-trifluoromethylphenyl)amino]imidazoline hydrochloride 
• 1269603-82-8 (4S)-4-(N-benzyloxycarbonyl-2-aminoethyl)-2-[(3-trifluoromethylphenyl)amino]imidazoline 
• 65069-76-3 S-methyl-3-(trifluoromethyl)phenylisothiourea hydroiodide 

Relevant articles and documents

4-PHENYL-N-(PHENYL)THIAZOL-2-AMINE DERIVATIVES AND RELATED COMPOUNDS AS ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS FOR THE TREATMENT OF E.G. ANGIOGENESIS IMPLICATED OR INFLAMMATORY DISORDERS

4-phenyl-N-(phenyl)thiazol-2-amine and 4-(pyridin-3-yl)-N-( phenyl) thiazol-2-amine derivatives and the corresponding thiadiazole, thiophene, oxazole, oxadiazole, imidazole and triazole derivatives and related compounds as aryl hydrocarbon receptor (AHR) agonists for the treatment of angiogenesis implicated disorders, such as e.g. retinopathy, psoriasis, rheumatoid arthritis, obesity and cancer, or inflammatory disorders.

Effect of N-1 arylation of monastrol on kinesin Eg5 inhibition in glioma cell lines

An original and focused library of two sets of dihydropyrimidin-2-thiones (DHPMs) substituted with N-1 aryl groups derived from monastrol was designed and synthesized in order to discover a more effective Eg5 ligand than the template. Based on molecular docking studies, four ligands were selected to perform pharmacological investigations against two glioma cell lines. The results led to the discovery of two original compounds, called 20h and 20e, with an anti-proliferative effects, achieving IC50 values of about half that of the IC50 of monastrol in both cell lines. As with monastrol, flow cytometry analyses showed that the 20e and 20h compounds induced cell cycle arrest in the G2/M phase, and immunocytochemistry essays revealed the formation of monopolar spindles due to Eg5 inhibition without any toxicity to Caenorhabditis elegans.

Palladium and Lewis-Acid-Catalyzed Intramolecular Aminocyanation of Alkenes: Scope, Mechanism, and Stereoselective Alkene Difunctionalizations

An expansion of methodologies aimed at the formation of versatile organonitriles, via the intramolecular aminocyanation of unactivated alkenes, is herein reported. Importantly, the need for a rigid tether in these reactions has been obviated. The ease-of-synthesis and viability of substrates bearing flexible backbones has permitted for diastereoselective variants as well. We demonstrated the utility of this methodology with the formation of pyrrolidones, piperidinones, isoindolinones, and sultams. Furthermore, subsequent transformation of these motifs into medicinally relevant molecules is also demonstrated. A double crossover 13C-labeling experiment is consistent with a fully intramolecular cyclization mechanism. Deuterium labeling experiments support a mechanism involving syn-addition across the alkene.

Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against: Klebsiella pneumoniae

A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712). Some of the synthesized compounds exhibited synergistic activity. When 4 μg ml-1 compound B1 was combined with PB, it showed potent antibacterial activity, achieving 64-fold reduction of the MIC of PB. Furthermore, compound B1 showed prominent synergistic efficacy in both concentration gradient and time-kill curves in vitro. In addition, B1 combined with PB also exhibited synergistic and partial synergistic effect against E. coli (ATCC25922 and its clinical isolates), Acinetobacter baumannii (ATCC19606 and its clinical isolates), and Pseudomonas aeruginosa (Pae-1399).

Synthesis and antitumor evaluation of 5-(benzo[: D] [1,3]dioxol-5-ylmethyl)-4-(tert -butyl)- N -arylthiazol-2-amines

A series of novel N-aryl-5-(benzo[d][1,3]dioxol-5-ylmethyl)-4-(tert-butyl)thiazol-2-amines (C1-C31) were synthesized and evaluated for their antitumor activities against HeLa, A549 and MCF-7 cell lines. Some tested compounds showed potent growth inhibition properties with IC50 values generally below 5 μM against the three human cancer cells lines. Compound C27 showed potent activities against HeLa and A549 cell lines with IC50 values of 2.07 ± 0.88 μM and 3.52 ± 0.49 μM, respectively. Compound C7 (IC50 = 2.06 ± 0.09 μM) was the most active compound against A549 cell line, while compound C16 (IC50 = 2.55 ± 0.34 μM) showed the best inhibitory activity against the MCF-7 cell line. The preliminary mechanism of the inhibitory effect was investigated via further experiments, such as morphological analysis by dual AO/EB staining and Hoechst 33342 staining, and cell apoptosis and cycle assessment by FACS analysis. The results illustrated that compound C27 could induce apoptosis and cause both S-phase and G2/M-phase arrests in HeLa cell line. Therefore, compound C27 could be developed as a potential antitumor agent.

With anti-tumor activity of the amide compound and use thereof

The invention belongs to the technical field of medicines and particularly relates to amide compounds with antitumor activity and an application of the amide compounds. The amide compounds are as shown in the general formula (I), wherein R1 and R2 can be same or different and are respectively and independently selected from hydrogen, halogen, a cyan, hydroxyl, halogenated alkyl, alkoxy, alkoxylalkyl, alkylamino or alkylaminoalkyl; R3 is triazole, 1, 3, 4-oxa-diazole, carbonyl and respective corresponding electro-withdrawing or electron donating substituent groups; and X is carbon or nitrogen atoms. A pharmacological activity result of the amide compounds provided by the invention shows that the amide compounds have favorable inhibiting effect for tumor cell strains.

Probing the ATP-Binding Pocket of Protein Kinase DYRK1A with Benzothiazole Fragment Molecules

DYRK1A has emerged as a potential target for therapies of Alzheimer's disease using small molecules. On the basis of the observation of selective DYRK1A inhibition by firefly d-luciferin, we have explored static and dynamic structural properties of fragment sized variants of the benzothiazole scaffold with respect to DYRK1A using X-ray crystallography and NMR techniques. The compounds have excellent ligand efficiencies and show a remarkable diversity of binding modes in dynamic equilibrium. Binding geometries are determined in part by interactions often considered "weak", including "orthogonal multipolar" types represented by, for example, F-CO, sulfur-aromatic, and halogen-aromatic interactions, together with hydrogen bonds that are modulated by variation of electron withdrawing groups. These studies show how the benzothiazole scaffold is highly promising for the development of therapeutic DYRK1A inhibitors. In addition, the subtleties of the binding interactions, including dynamics, show how full structural studies are required to fully interpret the essential physical determinants of binding.

Heterocyclic compounds useful for kinase inhibition

Provided herein are compounds useful for kinase inhibition.

Synthesis and Cytotoxicity in Vitro of N-Aryl-4-(Tert-butyl)-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine

A series of novel N-aryl-4-(tert-butyl)-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amines were synthesized in a green way. H2O2-NaBr Brominating circulatory system was used in the synthesis of the key intermediate in a mild condition. All of the target compounds were confirmed by1H NMR and elemental analysis and tested for their cytotoxicity against two different human cancer cell lines. The cytotoxicity assay revealed that some of the title compounds showed moderate to strong cytotoxic activities. Compound 2i was the most potent compound with the IC50 values of 9 μMagainst Hela cells and 15 μMagainst Bel-7402 cells, respectively.

Structure-activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis

A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl) -1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 μM or 0.008 μg/mL in 7H9 media and therapeutic index of nearly ～300. However, 55 is rapidly metabolized by human liver microsomes (t1/2 = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of ～10-5.