1516-37-6

Usage

Uses

Used in Pharmaceutical Industry:
(2-Methoxyphenyl)thiourea is used as an intermediate in the synthesis of various pharmaceutical compounds for [application reason]. Its sulfur-containing structure allows for the development of new drugs with specific therapeutic properties, making it a valuable component in the design and production of novel medications.
Used in Chemical Synthesis:
In the chemical industry, (2-Methoxyphenyl)thiourea is used as a building block or reagent in the synthesis of a wide range of organic compounds. Its unique structure enables the creation of new molecules with diverse applications, from agrochemicals to specialty chemicals.
Used in Research and Development:
(2-Methoxyphenyl)thiourea is also utilized in research and development settings, where it serves as a model compound for studying the properties and reactivity of sulfur-containing compounds. This helps scientists better understand the behavior of thioureas and their potential applications in various fields.
Used in Analytical Chemistry:
As a white solid with distinct chemical properties, (2-Methoxyphenyl)thiourea can be employed in analytical chemistry for the development of new methods and techniques for the detection and quantification of sulfur-containing compounds. This can be particularly useful in environmental monitoring and quality control processes.

InChI:InChI=1/C8H10N2OS/c1-11-7-5-3-2-4-6(7)10-8(9)12/h2-5H,1H3,(H3,9,10,12)

Upstream product

• 3288-04-8 1-isothiocyanato-2-methoxybenzene 
• 1147550-11-5 ammonium thiocyanate 
• 90-04-0 2-methoxy-phenylamine 
• 333-20-0 potassium thioacyanate 
• 53662-51-4 (2-methoxy-phenyl)-dithiocarbamic acid ; compound with triethylamine 
• 65195-61-1 N-(2-methoxyphenyl)cyanamide 
• 14327-07-2 N-(2-Methoxy-phenyl)-N'-(tert.-butyl)-thioharnstoff 
• 540-72-7 sodium thiocyanide 
• 134-29-2 2-methoxyaniline hydrochloride 
• 1226-64-8 1,3-bis-(2-methoxy-phenyl)-thiourea 
• 21258-10-6 N-benzoyl- N′-(2-methoxyphenyl)thiourea 

Downstream Products

• 7478-44-6 N,N''-bis-(2-methoxy-phenyl)-S,S'-ethanediyl-bis-isothiourea; dihydrobromide 
• 2327-19-7 (2-methoxy-phenyl)-(4-methyl-thiazol-2-yl)-amine 
• 104510-07-8 (4,5-dimethyl-thiazol-2-yl)-(2-methoxy-phenyl)-amine 
• 132981-88-5 2-o-anisidino-5-phenyl-thiazol-4-one 
• 5464-79-9 4-methoxy-1,3-benzothiazol-2-amine 
• 67618-12-6 2-Amino-7-chloro-4-methoxybenzothiazole 
• 61889-50-7 (2-methoxy-phenyl)-(4-pyridin-3-yl-thiazol-2-yl)-amine 
• 31102-87-1 3-(2-methoxy-phenyl)-6-nitro-3H-thiazolo[4,5-b]quinoxalin-2-ylideneamine 
• 31102-74-6 (2-methoxy-phenyl)-(6-nitro-thiazolo[4,5-b]quinoxalin-2-yl)-amine 
• 16238-40-7 2-(2-methoxy-anilino)-4-oxo-4H-[1,3]thiazine-6-carboxylic acid methyl ester 
• 3338-13-4 (2-methoxy-phenyl)-(4,6,6-trimethyl-6H-[1,3]thiazin-2-yl)-amine 
• 78864-06-9 [5-(4-fluoro-phenyl)-thiazol-2-yl]-(2-methoxy-phenyl)-amine 
• 31102-90-6 7-chloro-3-(2-methoxy-phenyl)-3H-thiazolo[4,5-b]quinoxalin-2-ylideneamine 
• 31102-77-9 (7-chloro-thiazolo[4,5-b]quinoxalin-2-yl)-(2-methoxy-phenyl)-amine 

Relevant academic research and scientific papers

Search for the Active Ingredients from a 2-Aminothiazole DMSO Stock Solution with Antimalarial Activity

Chemical decomposition of DMSO stock solutions is a common incident that can mislead biological screening campaigns. Here, we share our case study of 2-aminothiazole 1, originating from an antimalarial class that undergoes chemical decomposition in DMSO at room temperature. As previously measured biological activities observed against Plasmodium falciparum NF54 and for the target enzyme PfIspE were not reproducible for a fresh batch, we tackled the challenge to understand where the activity originated from. Solvent- and temperature-dependent studies using HRMS and NMR spectroscopy to monitor the decomposition led to the isolation and in vitro evaluation of several fractions against PfIspE. After four days of decomposition, we successfully isolated the oxygenated and dimerised compounds using SFC purification and correlated the observed activities to them. Due to the unstable nature of the two isolates, it is likely that they undergo further decomposition contributing to the overall instability of the compound.

Scalable synthesis and antibacterial evaluation of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles

A new series of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles was synthesized via a one-pot efficient and scalable method, involving the condensation of 2-aminobenzothiazoles derivatives, substituted anilines, and chlorosulfonyl isocyanate. The products were obtained in good yield with a simple workup, and their structures were confirmed from their spectral analyses. The synthesized compounds were further screened for their antibacterial activity against Gram-positive and Gram-negative pathogenic strains. The molecules show promising activity in the MIC value range of 2–0.25 μg/ml against selected bacterial strains, especially against nonfermentative carbapenem-resistant bacteria (Pseudo VIM-2 and Acinetobacter baumanni).

Synthesis of thiazolone derivatives as novel soybean 15-LOX inhibitors

Background: Thiazole derivatives are known as important sulfur containing heterocycles which are present in a wide range of biologically active natural products. Methods: A series of thiazolone derivatives were synthesized and evaluated for their soybean 15-LOX inhibitory activity. The title compounds were prepared by the reaction of 2-arylthiazol-4(5H)-ones and different aromatic aldehydes. All compounds were characterized and evaluated against soybean 15-LOX. Results: Among the synthesized thiazolone derivatives, 5-(4-methoxybenzylidene)-2-((2-methoxyphenyl) amino)thiazol-4(5H)-one (3l) was found to be the most active compound comparing with quercetin as the reference drug. Conclusion: It seems that prepared thiazolones having methoxy groups both on aryl and aminoaryl moieties can be considered for further drug discovery research.

BENZOTHIAZOLE DERIVATIVE AND ANTI-TUMOR USE THEREOF

The present invention relates to a benzothiazole derivative of formula 1 or a pharmaceutically acceptable salt thereof and a process for preparation thereof. The present invention also relates to a pharmaceutical composition comprising the compounds and the use of the compounds in the preparation of an anti-tumor medicament.

Facile synthesis, molecular docking and toxicity studies of 4-Phenyl-3-phenylamino-4H-[1,2,4]thiadiazol-5-one analogs as GABAA receptor agonists

A series of 4-Phenyl-3-phenylamino-4H-[1,2,4]thiadiazol-5-one derivatives was synthesized by a simple method and their structures were established by physical and spectroscopic methods like infrared, mass and nuclear magnetic resonance spectroscopy. Elemental formulae of all the compounds were determined by elemental analysis and compared with the calculated value. Log P value and in vitro hydrolysis, in simulated gastric fluid and simulated intestinal fluid, for all the compounds were determined by standard methods. Synthesized 1, 2, 4-thiadiazolines were screened for their anticonvulsant activity against maximal electroshock method and isoniazid induced seizures. All the compounds showed good anticonvulsant activity. The compound 4-(3,4-dichloro-phenyl)-3-(3,4-dichloro-phenylamino)-4H-[1,2,4]thiadiazol-5-one (3a) was found to be the most potent member of the series. Molecular docking studies of the synthesized compounds depicted their stable ligand–receptor complex conformation with the typical binding pocket of γ-aminobutyric acid A receptor protein. Compound 3a confined its effect in the molecular docking studies also with non-covalent interactions with Tyr 157, Phe 200 and Tyr 205, the key interacting residues of γ-aminobutyric acid A receptor protein 4COF. In silico absorption, distribution, metabolism and elimination performance of all the compounds also appear to favour anticonvulsant effect. “LAZAR” and “OSIRIS” property explorer predicted nontoxic, nonmutagenic, noncarcinogenic, etc. nature for all the compounds. In conclusion, some γ-aminobutyric acid A receptor agonists have been synthesized in this study with promising drug-like properties, which merit further development.

Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists

Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by assessment of active derivatives on STZ-induced diabetic model. It was observed that nine of twenty novel piperine analogues (5b, 6a-h), showed significantly higher antidiabetic activity in comparison with rosiglitazone (standard). Furthermore, these active derivatives were evaluated for their action as PPAR-γ agonists demonstrating their mechanism of action. The effects on body weight, lipid peroxidation, and hepatotoxicity after administration with active derivatives were also studied to further establish these derivatives as lead molecules for treatment of diabetes with lesser side-effects.

Formation of 1,4,2-Dithiazolidines or 1,3-Thiazetidines from 1,1-Dichloro-2-nitroethene and Phenylthiourea Derivatives

A method for preparation of 1,4,2-dithiazolidine or 1,3-thiazetidine heterocycles was developed by reactions of phenylthioureas with 1,1-dichloro-2-nitroethene. The solvent has a significant influence on the type of product formation. 1,4,2-Dithiazolidines were formed in the aprotic solvent chloroform, while in the protic solvent ethanol, 1,3-thiazetidines were the main products.

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.

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.

Synthesis and biological evaluation of 2-phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-ones as IKK2 inhibitors

In a search for novel molecules to treat inflammatory disorders, we identified several compounds with inhibitory action against the IKK2 enzyme using in silico methods. Based on the virtual hit of compounds 1 and 2, a novel series of 2-phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-one derivatives was designed, synthesized, and evaluated for IKK2 inhibitory activity. Among the synthesized derivatives, compounds 17f and 19f showed good IKK2 inhibitory potency, which have 4-carboxaminophenyl on the 2-furan ring and a methoxy group on the phenylimino moiety at the 2-position of the core structure. The most potent compound was 2-(2,4-dimethoxyphenyl)imino-5((5(4-carboxaminophenyl)furan-2-yl)methylene)thiazolidin-4-one (19f, IC50 = 0.94 μM), which represents a synergic effect of the two virtual hit compounds against IKK2. We also identified compounds showing inhibitory activities against interleukin (IL)-17, CCK-8, and tumor necrosis factor-alpha (TNF-α), which are NF-κB-dependent pro-inflammatory cytokine mediators.