106663-84-7

Basic information

• Product Name: bis(2-(N-phenylcarboxamido)phenyl)diselenide
• Synonyms: bis(2-(N-phenylcarboxamido)phenyl)diselenide
• CAS NO: 106663-84-7
• Molecular Formula: C₂₆H₂₀N₂O₂Se₂
• Molecular Weight: 550.3692
• Mol File: 106663-84-7.mol
• Article Data: 19

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: bis(2-(N-phenylcarboxamido)phenyl)diselenide(CAS DataBase Reference)
• NIST Chemistry Reference: bis(2-(N-phenylcarboxamido)phenyl)diselenide(106663-84-7)
• EPA Substance Registry System: bis(2-(N-phenylcarboxamido)phenyl)diselenide(106663-84-7)

Safety Data

• Hazardous Substances Data: 106663-84-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C26H20N2O2Se2/c29-25(27-19-11-3-1-4-12-19)21-15-7-9-17-23(21)31-32-24-18-10-8-16-22(24)26(30)28-20-13-5-2-6-14-20/h1-18H,(H,27,29)(H,28,30)

Upstream product

• 93-98-1 N-phenyl benzoyl amide 
• 60940-34-3 2-phenyl-1,2-benzoisoselenazol-3(2H)-one 
• 100-53-8 phenylmethanethiol 
• 104473-83-8 2-phenyl-1,2-benzioselenazol-3(2H)-one selenoxide 
• 104030-64-0 C₁₅H₁₅NOSSe 
• 114744-69-3 S-(2-phenyl carbamoyl benzeneselenenyl)benzylmercaptan 
• 139015-80-8 N-phenyl-2-carboxamidobenzene selenol 
• 101562-89-4 S-(2-phenyl carbamoyl benzeneselenenyl)-glutathione 
• 70-18-8 GLUTATHIONE 
• 15310-01-7 benodanil 
• 2099-63-0 anthranilic acid hydrochloride 
• 105893-07-0 2,2’-diselanediyldibenzoyl chloride 
• 62-53-3 aniline 
• 1441-85-6 2-(chloroseleno)benzoyl chloride 

Downstream Products

• 60940-34-3 2-phenyl-1,2-benzoisoselenazol-3(2H)-one 
• 60940-24-1 2-methylseleno-N-phenylbenzamide 
• 356761-43-8 ebselen seleninic acid 
• 104473-83-8 2-phenyl-1,2-benzioselenazol-3(2H)-one selenoxide 
• 60940-33-2 2-benzylbenzo[d][1,2]selenazol-3(2H)-one 
• 104473-79-2 2-benzyl-1,2-benzisoselenazol-3(2H)-one-Se-oxide 

Relevant articles and documents

A novel redox reaction of ebselen with alcohol in basic solution

Ebselen is an organoselenium compound that exhibits a glutathione peroxidase-like activity. The kinetics of ebselen degradation in basic aqueous solution containing primary alcohol was investigated by HPLC. The reversible reaction of ebselen and its dimer (diselenide) was discovered as a novel redox reaction. This reaction followed first-order degradation in basic solution at a constant temperature, and the equilibrium constants of ebselen and diselenide depended on pH. Analysis of the degradation rate for the forward reaction-pH profile indicated that specific base catalysis occurs in ebselen. The mechanism of this redox reaction was investigated by HPLC, spectrophotometry and trapping the labile intermediate with trichloroethylene. Ebselen decomposes to diselenide via selenenic acid and selenol by reacting with primary alcohol. The deuterium isotope effect on the forward reaction indicated that the reaction rate depends on the strength of the hydrogen-carbon bond at the α-position of primary alcohol. On the other hand, the effect of nitrogen replacement on the reverse reaction showed that diselenide is converted into ebselen by oxidation with oxygen existing in the solution.

Water-dependent synthesis of biologically active diaryl diselenides

A new one-step method for the synthesis of diaryl diselenides has been developed. The reaction of o-iodobenzamides with dilithium diselenide can be controlled by the presence of water providing a simple and efficient protocol to obtain benzisoselenazolones or diaryl diselenides. A series of N-Aryl ebselen derivatives and the corresponding diselenides was obtained. All synthesized compounds were tested in vitro as antioxidants and cytotoxic agents. N-(2,3,4-Trimethoxyphenyl)benzisoselenazol-3(2H)-one was the best in vitro antioxidant and the corresponding diselenide the most potent cytotoxic agent against prostate cancer cell line DU145, being inactive towards healthy prostate cell line PNT1A. Formula parented.

1,2-Benzisoselenazol-3(2H)-one Derivatives As a New Class of Bacterial Urease Inhibitors

Urease inhibitors are considered promising compounds for the treatment of ureolytic bacterial infections, particularly infections resulting from Helicobacter pylori in the gastric tract. Herein, we present the synthesis and the inhibitory activity of novel and highly effective organoselenium compounds as inhibitors of Sporosarcina pasteurii and Helicobacter pylori ureases. These studied compounds represent a class of competitive reversible urease inhibitors. The most active compound, 2-phenyl-1,2-benzisoselenazol-3(2H)-one (ebselen), displayed Kivalues equal to 2.11 and 226 nM against S. pasteurii and H. pylori enzymes, respectively, indicating ebselen as one of the most potent low-molecular-weight inhibitors of bacterial ureases reported to date. Most of these molecules penetrated through the cell membrane of the Gram-negative bacteria Escherichia coli (pGEM::ureOP) in vitro. Furthermore, whole-cell studies on the H. pylori J99 reference strain confirmed the high efficiency of the examined organoselenium compounds as urease inhibitors against pathogenic bacteria.

Mechanistic investigations on the efficient catalytic decomposition of peroxynitrite by ebselen analogues

In this study, ebselen and its analogues are shown to be catalysts for the decomposition of peroxynitrite (PN). This study suggests that the PN-scavenging ability of selenenyl amides can be enhanced by a suitable substitution at the phenyl ring in ebselen