106663-84-7

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 
• 126543-42-8 2-benzylseleno-N-phenylbenzamide 
• 60940-34-3 2-phenyl-1,2-benzoisoselenazol-3(2H)-one 
• 62-53-3 aniline 
• 70-18-8 GLUTATHIONE 
• 1441-85-6 2-(chloroseleno)benzoyl chloride 
• 105893-07-0 2,2’-diselanediyldibenzoyl chloride 
• 2099-63-0 anthranilic acid hydrochloride 
• 15310-01-7 benodanil 
• 118-92-3 anthranilic acid 
• 6512-83-0 2,2'-diselanediyl-di-benzoic acid 
• 101562-89-4 S-(2-phenyl carbamoyl benzeneselenenyl)-glutathione 
• 139015-80-8 N-phenyl-2-carboxamidobenzene selenol 
• 114744-69-3 S-(2-phenyl carbamoyl benzeneselenenyl)benzylmercaptan 

Downstream Products

• 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 
• 104473-83-8 2-phenyl-1,2-benzioselenazol-3(2H)-one selenoxide 
• 60940-34-3 2-phenyl-1,2-benzoisoselenazol-3(2H)-one 
• 60940-24-1 2-methylseleno-N-phenylbenzamide 
• 356761-43-8 ebselen seleninic acid 

Relevant academic research and scientific papers

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.

N-phenyl-2-(triphenylstannylseleno)benzamide and 2-methylseleno-N-phenylbenzamide

The two independent molecules of N-phenyl-2-(triphenylstannylseleno)benzamide, C31H25NOSeSn, differ significantly in the conformations of the N-phenylbenzamide groups. For 2-methylseleno-N-phenylbenzamide, C14H13/sub

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.

Identification of methionine aminopeptidase 2 as a molecular target of the organoselenium drug ebselen and its derivatives/analogues: Synthesis, inhibitory activity and molecular modeling study

A collection of twenty-six organoselenium compounds, ebselen and its structural analogues, provided a novel approach for inhibiting the activity of human methionine aminopeptidase 2 (MetAP2). This metalloprotease, being responsible for the removal of the amino-terminal methionine from newly synthesized proteins, plays a key role in angiogenesis, which is essential for the progression of diseases, including solid tumor cancers. In this work, we discovered that ebselen, a synthetic organoselenium drug molecule with anti-inflammatory, anti-oxidant and cytoprotective activity, inhibits one of the main enzymes in the tumor progression pathway. Using three-step synthesis, we obtained twenty-five ebselen derivatives/analogues, ten of which are new, and tested their inhibitory activity toward three neutral aminopeptidases (MetAP2, alanine and leucine aminopeptidases). All of the tested compounds proved to be selective, slow-binding inhibitors of MetAP2. Similarly to ebselen, most of its analogues exhibited a moderate potency (IC50= 1–12 μM). Moreover, we identified three strong inhibitors that bind favorably to the enzyme with the half maximal inhibitory concentration in the submicromolar range.

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.

Computer-assisted designed "selenoxy-chinolin": A new catalytic mechanism of the GPx-like cycle and inhibition of metal-free and metal-associated Aβ aggregation

Using support from rational computer-assisted design, a novel series of hybrids (selenoxy-chinolin) designed by fusing the metal-chelating agent CQ and the antioxidant ebselen were synthesized and evaluated as multitarget-directed ligands. Most of the hybrids demonstrated significant ability to mimic GPx, which is highly consistent with the prediction results of DFT studies for the selenenyl sulfide intermediates in the computational design. Using 77Se, 1H and 13C NMR spectroscopy and high-resolution mass spectroscopy (HRMS), a novel catalytic mechanism, including a new selenium quinone active species, was first demonstrated. 2D NMR studies indicated that the typical hybrid has an effective interaction with Aβ. In addition, the optimal compound 12k was found to possess an excellent ability to scavenge peroxide and to inhibit self- and metal-induced Aβ aggregation, and an ability to disassemble preformed self- and metal-induced Aβ aggregates effectively. Furthermore, 12k was able to penetrate the central nervous system (CNS) and did not exhibit any acute toxicity in mice at doses up to 2000 mg kg-1. Overall, we demonstrated that hybrid 12k, through rational structure-based computational design, shows a potential for development as a therapeutic agent in AD.

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

Crucial role of selenium in the virucidal activity of benzisoselenazol- 3(2h)-ones and related diselenides

Various N-substituted benzisoselenazol-3(2H)-ones and their non-seleniumcontaining analogues have been synthesized and tested against selected viruses (HHV-1, EMCV and VSV) to determine the extent to which selenium plays a role in antiviral activity. The data presented here show that the presence of selenium is crucial for the antiviral properties of benzisoselenazol-3(2H)-ones since their isostructural analogues having different groups but lacking selenium either did not show any antiviral activity or their activity was substantially lower. The open-chain analogues of benzisoselenazol- 3(2H)-ones-diselenides also exhibited high antiviral activity while selenides and disulfides were completely inactive towards model viruses.

Antioxidant activity of the anti-inflammatory compound ebselen: A reversible cyclization pathway via selenenic and seleninic acid intermediates

A revised mechanism that accounts for the glutathione peroxidase (GPx)-like catalytic activity of the organoselenium compound ebselen is described. It is shown that the reaction of ebselen with H2O2 yields seleninic acid as the only oxidized product. The X-ray crystal structure of the seleninic acid shows that the selenium atom is involved in a noncovalent interaction with the carbonyl oxygen atom. In the presence of excess thiol, the Se-N bond in ebselen is readily cleaved by the thiol to produce the corresponding selenenyl sulfide. The selenenyl sulfide thus produced undergoes a disproportionate in the presence of H2O2 to produce the diselenide, which upon reaction with H2O2, produces a mixture of selenenic and seleninic acids. The addition of thiol to the mixture containing selenenic and seleninic acids leads to the formation of the selenenyl sulfide. When the concentration of the thiol is relatively low in the reaction mixture, the selenenic acid undergoes a rapid cyclization to produce ebselen. The seleninic acid, on the other hand, reacts with the diselenide to produce ebselen as the final product. DFT calculations show that the cyclization of selenenic acids to the corresponding selenenyl amides is more favored than that of sulfenic acids to the corresponding sulfenyl amides. This indicates that the regeneration of ebselen under a variety of conditions protects the selenium moiety from irreversible inactivation, which may be responsible for the biological activities of ebselen.

Nucleophilic cleavage of selenaheterocyclic ring in benzisoselenazol-3(2H)- ones and 1,3,2-benzodiselenazoles

The reactions of cyclic selenenamides: benzisoselenazol-3(2H)-ones and 1,3,2-benzo-diselenazoles 3 with living cell nucleophiles such as water and thiols were investigated. Both of them caused Se-N bond cleavage. The thiolysis of 1 led to selenosulphides