1736-72-7

Usage

Uses

Used in Pharmaceutical Synthesis:
1-[4-(TRIFLUOROMETHYL)PHENYL]-2-THIOUREA is used as a reagent for the synthesis of thiourea analogs, which are known to act as inhibitors of UT-A and UT-B transporters. These transporters play a crucial role in the regulation of water and electrolyte balance in the body, and their inhibition can have therapeutic applications in certain medical conditions.
Additionally, 1-[4-(TRIFLUOROMETHYL)PHENYL]-2-THIOUREA is also used in the synthesis of 2-aminothiazole sphingosine inhibitors. These compounds have potential applications in the treatment of various diseases, including cancer, by targeting specific cellular pathways and processes.

Upstream product

• 455-14-1 4-trifluoromethylphenylamine 
• 117174-71-7 N-((4-trifluoromethylphenyl)thiocarbamoyl)benzamide 
• 1147550-11-5 ammonium thiocyanate 
• 90774-69-9 4-aminobenzotrifluoride hydrochloride 
• 333-20-0 potassium thioacyanate 
• 1645-65-4 4-(trifluoromethyl)phenyl isothiocyanate 
• 1226922-10-6 C₆H₁₅N*C₈H₆F₃NS₂ 
• 1430796-50-1 C₈H₆F₃NS₂*C₆H₁₂N₂ 
• 540-72-7 sodium thiocyanide 
• 45943-14-4 benzoyl isothiocyanate 

Downstream Products

• 119125-43-8 2-Methyl-1-(4-trifluoromethyl-phenyl)-isothiourea; hydriodide 
• 777-12-8 2-amino-6-trifluoromethyl-1,3-benzothiazole 
• 643013-14-3 4-(4-chlorophenyl)-N-(4-(trifluoromethyl)phenyl)thiazol-2-amine 
• 1095824-45-5 C₁₃H₁₁F₃N₂O₂S 
• 696628-76-9 4-(4-pyridinyl)-N-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine 
• 1166390-18-6 4-(trifluoromethyl)phenylthiourea acrylamide 
• 1214888-50-2 C₁₈H₁₂ClF₃N₂O₂S 

Relevant academic research and scientific papers

Discovery of aminothiazole derivatives as novel human enterovirus A71 capsid protein inhibitors

Enterovirus A71 (EV-A71), one of the major pathogens that causes hand, foot and mouth disease (HFMD), has seriously threatened the health and safety of young children. In this study, aminothiazole derivatives were synthesized and screened against EV-A71 in Rhabdomyosarcoma (RD) cells. The best compound (12s), with a biphenyl group, showed activity against EV-A71 (EC50: 0.27 μM) but also against a series of different human enteroviruses without significant cytotoxicity (CC50 > 56.2 μM). Mechanistic studies including time-of-drug-addition assays, viral entry assays and microscale thermophoresis (MST) experiments, showed that 12s binds to EV-A71 capsid and blocks the binding between the viral protein VP1 and the relevant human scavenger receptor class B member 2 (hSCARB2).

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.

Novel arylimino thiazole compound, preparation method and uses thereof

The present invention relates to a compound with antibacterial synergy activity, a preparation and uses thereof, particularly to a novel arylimino thiazole compound, a preparation method and uses thereof, and specifically discloses a class of compounds represented by a formula (I) or optical isomers, cis-trans isomers or pharmaceutically acceptable salts thereof, a preparation method and uses thereof. The invention further discloses a pharmaceutical composition containing the compound. The compound of the present invention can effectively enhance the antibacterial activity of antibiotics, andcan be used for treating antibiotic-resistant bacteria. The formula (I) is defined in the specification.

2-(4-trifluoromethyl-phenylimino)-5-(2-naphthyl)methylene-thiazolidin-4-one compound and application thereof

The invention discloses a thiazole heterocyclic compound. The thiazole heterocyclic compound is 2-(4-trifluoromethyl-phenylimino)-5-(2-naphthyl) methylene-thiazolidin-4-one compound, which is referred as TNTO and has a chemical structure as shown in a general formula (I). The invention further discloses an application of the compound as an aromatic hydrocarbon receptor stimulant. Experiments prove that the thiazole heterocyclic compound under the concentration of 10 muM can remarkably up-regulate the gene, protein expression of the related exogenous substance metabolic enzyme CYP1A1 of the downstream target gene of the aromatic hydrocarbon receptor in the mouse liver cancer cells, the compound is prompted to be an agonist of an aromatic hydrocarbon receptor, and is expected to become a potential medicine which takes the aromatic hydrocarbon receptor as the tumor target, and has wide clinical application prospect and economic development value.

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).

Aminothiazole derivatives

The invention relates to aminothiazole heterocyclic derivatives, a preparation method thereof and an application of the aminothiazole heterocyclic derivatives in preparation of drugs for treating or preventing progressive cognitive disorder and/or amnesia diseases.

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.

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.

Design, synthesis, X-ray crystallographic analysis, and biological evaluation of thiazole derivatives as potent and selective inhibitors of human dihydroorotate dehydrogenase

Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.

Multi-dimensional target profiling of N,4-diaryl-1,3-thiazole-2-amines as potent inhibitors of eicosanoid metabolism

Eicosanoids like leukotrienes and prostaglandins play a considerable role in inflammation. Produced within the arachidonic acid (AA) cascade, these lipid mediators are involved in the pathogenesis of pain as well as acute and chronic inflammatory diseases like rheumatoid arthritis and asthma. With regard to the lipid cross-talk within the AA pathway, a promising approach for an effective anti-inflammatory therapy is the development of inhibitors targeting more than one enzyme of this cascade. Within this study, thirty N-4-diaryl-1,3-thiazole-2- amine based compounds with different substitution patterns were synthesized and tested in various cell-based assays to investigate their activity and selectivity profile concerning five key enzymes involved in eicosanoid metabolism (5-, 12-, 15-lipoxygenase (LO), cyclooxygenase-1 and -2 (COX-1/-2)). With compound 7, 2-(4-phenyl)thiazol-2-ylamino)phenol (ST-1355), a multi-target ligand targeting all tested enzymes is presented, whereas compound 9, 2-(4-(4-chlorophenyl)thiazol-2-ylamino)phenol (ST-1705), represents a potent and selective 5-LO and COX-2 inhibitor with an IC50 value of 0.9 ± 0.2 μM (5-LO) and a residual activity of 9.1 ± 1.1% at 10 μM (COX-2 product formation). The promising characteristics and the additional non-cytotoxic profile of both compounds reveal new lead structures for the treatment of eicosanoid-mediated diseases.