897340-70-4

Basic information

• Product Name: (5E)-5-(3,4-dihydroxybenzylidene)-2-mercapto-3-phenyl-3,5-dihydro-4H-imidazol-4-one
• Synonyms: (5E)-5-(3,4-dihydroxybenzylidene)-2-mercapto-3-phenyl-3,5-dihydro-4H-imidazol-4-one
• CAS NO: 897340-70-4
• Molecular Formula: C16H12N2O3S
• Molecular Weight: 312.34308
• Mol File: 897340-70-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 515.0±60.0 °C(Predicted)
• Appearance: /
• Density: 1.55±0.1 g/cm3(Predicted)
• PKA: 9.10±0.10(Predicted)
• CAS DataBase Reference: (5E)-5-(3,4-dihydroxybenzylidene)-2-mercapto-3-phenyl-3,5-dihydro-4H-imidazol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5E)-5-(3,4-dihydroxybenzylidene)-2-mercapto-3-phenyl-3,5-dihydro-4H-imidazol-4-one(897340-70-4)
• EPA Substance Registry System: (5E)-5-(3,4-dihydroxybenzylidene)-2-mercapto-3-phenyl-3,5-dihydro-4H-imidazol-4-one(897340-70-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 897340-70-4(Hazardous Substances Data)

Usage

General Description

The chemical compound "(5E)-5-(3,4-dihydroxybenzylidene)-2-mercapto-3-phenyl-3,5-dihydro-4H-imidazol-4-one" is a heterocyclic compound with potential pharmacological properties. It contains a benzylidene moiety, a thiol group, and an imidazolone ring. (5E)-5-(3,4-dihydroxybenzylidene)-2-mercapto-3-phenyl-3,5-dihydro-4H-imidazol-4-one has shown potential as an antioxidant and as a potential therapeutic agent for various diseases. Its structure suggests that it may have the ability to scavenge free radicals and inhibit oxidative stress. Further research is needed to fully understand the biological and pharmacological properties of this compound.

Upstream product

• 2010-15-3 3-phenyl-2-thioxoimidazolidin-4-one 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 103-72-0 phenyl isothiocyanate 
• 2215-20-5 2-[(phenylcarbamothioyl)amino]acetic acid 

Relevant articles and documents

Design and evaluation of non-carboxylate 5-arylidene-2-thioxo-4-imidazolidinones as novel non-competitive inhibitors of protein tyrosine phosphatase 1B

Protein tyrosine phosphatase 1B (PTP1B) acts as a negative regulator of insulin and leptin signalling and is crucially involved in the development of type 2 diabetes mellitus, obesity, cancer and neurodegenerative diseases. Pursuing our efforts to identify PTP1B inhibitors endowed with drug-like properties, we designed and evaluated 3-aryl-5-arylidene-2-thioxo-4-imidazolidinones (7) as a novel class of non-carboxylate PTP1B inhibitors. In agreement with our design, kinetic studies demonstrated that selected compounds 7 act as reversible, non-competitive inhibitors of the target enzyme at low micromolar concentrations. Accordingly, molecular docking experiments suggested that these inhibitors can fit an allosteric site of PTP1B that we previously individuated. Moreover, cellular assays demonstrated that compound 7e acts as a potent insulin-sensitizing agent in human liver HepG2 cells. Taken together, our results showed that these non-competitive PTP1B inhibitors can be considered promising lead compounds aimed to enhance druggability of the target enzyme and identify novel antidiabetic drugs.

5-Arylidenethioxothiazolidinones as Inhibitors of Tyrosyl-DNA Phosphodiesterase i

Tyrosyl-DNA phosphodiesterase I (Tdp1) is a cellular enzyme that repairs the irreversible topoisomerase I (Top1)-DNA complexes and confers chemotherapeutic resistance to Top1 inhibitors. Inhibiting Tdp1 provides an attractive approach to potentiating clinically used Top1 inhibitors. However, despite recent efforts in studying Tdp1 as a therapeutic target, its inhibition remains poorly understood and largely underexplored. We describe herein the discovery of arylidene thioxothiazolidinone as a scaffold for potent Tdp1 inhibitors based on an initial tyrphostin lead compound 8. Through structure-activity relationship (SAR) studies we demonstrated that arylidene thioxothiazolidinones inhibit Tdp1 and identified compound 50 as a submicromolar inhibitor of Tdp1 (IC50 = 0.87 μM). Molecular modeling provided insight into key interactions essential for observed activities. Some derivatives were also active against endogenous Tdp1 in whole cell extracts. These findings contribute to advancing the understanding on Tdp1 inhibition.