27052-12-6

Basic information

• Product Name: 2-(4-METHOXY-PHENYLAMINO)-THIAZOL-4-ONE
• Synonyms: 2-(4-methoxyanilino)-1,3-thiazol-4-one
• CAS NO: 27052-12-6
• Molecular Formula: C₁₀H₁₀N₂O₂S
• Molecular Weight: 222.26
• Mol File: 27052-12-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 178.1-178.2 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 361.2 °C at 760 mmHg
• Flash Point: 172.3 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 2.1E-05mmHg at 25°C
• Refractive Index: 1.648
• PKA: 1.40±0.20(Predicted)
• CAS DataBase Reference: 2-(4-METHOXY-PHENYLAMINO)-THIAZOL-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-METHOXY-PHENYLAMINO)-THIAZOL-4-ONE(27052-12-6)
• EPA Substance Registry System: 2-(4-METHOXY-PHENYLAMINO)-THIAZOL-4-ONE(27052-12-6)

Safety Data

• Hazardous Substances Data: 27052-12-6(Hazardous Substances Data)

Usage

General Description

2-(4-Methoxy-phenylamino)-thiazol-4-one is a chemical compound with a molecular formula C10H9N3O2S. It is a thiazole derivative with a thiazol-4-one core structure and a 4-methoxyphenylamino group attached at the 2-position. 2-(4-Methoxy-phenylamino)-thiazol-4-one has potential applications in the field of medicinal chemistry, particularly in the development of pharmaceutical drugs. It may exhibit various pharmacological properties and biological activities, and its structure makes it a promising candidate for further research and development. Its synthesis, characterization, and potential uses in drug design and discovery make it of interest to chemists, pharmacologists, and other researchers in the field of drug development.

InChI:InChI=1/C10H10N2O2S/c1-14-8-4-2-7(3-5-8)11-10-12-9(13)6-15-10/h2-5H,6H2,1H3,(H,11,12,13)

Upstream product

• 105-39-5 chloroacetic acid ethyl ester 
• 2293-07-4 1-(4-methoxyphenyl)thiourea 
• 105-36-2 ethyl bromoacetate 
• 104-94-9 4-methoxy-aniline 
• 20949-66-0 2-methylsulfanyl-thiazol-4-one 
• 1147550-11-5 ammonium thiocyanate 
• 22303-36-2 N-(4-methoxyphenyl)-2-chloroacetamide 
• 21258-08-2 N-(4-anisyl)-N'-benzoylthiourea 

Downstream Products

• 1356945-69-1 2-[4-methoxyphenylimino]-5-(1H-pyridin-2-ylmethylidene)-1,3-thiazolidin-4-one 

Relevant articles and documents

Synthesis and exploration of configurational dynamics in equilibrating E/Z 2-aryliminothiazolidin-4-ones using NMR and estimation of thermodynamic parameters

In the present study, 2-aryliminothiazolidin-4-ones (3 and 5) were utilized as dynamic chemical systems, whose different states are modulated in a reversible fashion through specific chemical stimuli. The in-depth NMR investigation revealed that the magnitude of rotational energy barrier (ΔG?) is affected markedly by (1) the solvent polarity; (2) the electronic nature of the ring system present on the exocyclic CQN bond and (3) the temperature of the system. The derivatives of 5-(3-arylallylidene)-2-(arylimino)thiazolidin-4-one exist in two isomeric forms at room temperature in DMSO-d6: (2E,5Z,7E) ? (2Z,5Z,7E). The stereodynamics of the synthesized derivatives (5a-5t) has been investigated using variable temperature dynamic 1H-NMR (VT DNMR). The ΔG? values (≈15 kcal mol?1) estimated for the dynamic process depict a significant barrier between two forms in solution at ambient temperature. To go a step further, line shape analysis was also performed to get a clear understanding of the equilibration mechanism.

Design and microwave synthesis of new (5z) 5-arylidene-2-thioxo-1,3-thiazolinidin-4-one and (5z) 2-amino-5-arylidene-1,3-thiazol-4(5h)-one as new inhibitors of protein kinase dyrk1a

Here, we report on the synthesis of libraries of new 5-arylidene-2-thioxo-1,3-thiazolidin-4-ones 3 (twenty-two compounds) and new 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones 5 (twenty-four compounds) with stereo controlled Z-geometry under microwave irradi

A Library of Thiazolidin-4-one Derivatives as Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitors: An Attempt To Discover Novel Antidiabetic Agents

Protein tyrosine phosphatase 1B (PTP1B) is an important target for the treatment of diabetes. A series of thiazolidin-4-one derivatives 8–22 was designed, synthesized and investigated as PTP1B inhibitors. The new molecules inhibited PTP1B with IC50 values in the micromolar range. 5-(Furan-2-ylmethylene)-2-(4-nitrophenylimino)thiazolidin-4-one (17) exhibited potency with a competitive type of enzyme inhibition. structure–activity relationship studies revealed various structural facets important for the potency of these analogues. The findings revealed a requirement for a nitro group-including hydrophobic heteroaryl ring for PTP1B inhibition. Molecular docking studies afforded good correlation with experimental results. H-bonding and π–π interactions were responsible for optimal binding and effective stabilization of virtual protein-ligand complexes. Furthermore, in-silico pharmacokinetic properties of test compounds predicted their drug-like characteristics for potential oral use as antidiabetic agents.Additionally, a binding site model demonstrating crucial pharmacophoric characteristics influencing potency and binding affinity of inhibitors has been proposed, which can be employed in the design of future potential PTP1B inhibitors.