Ebselen

Base Information

• Chemical Name: Ebselen
• CAS No.: 60940-34-3
• Molecular Formula: C13H9NOSe
• Molecular Weight: 274.181
• Hs Code.: 29310099
• NSC Number: 757883,639762
• UNII: 40X2P7DPGH
• DSSTox Substance ID: DTXSID7045150
• Nikkaji Number: J22.968G
• Wikipedia: Ebselen
• Wikidata: Q5332073
• NCI Thesaurus Code: C65503
• Pharos Ligand ID: HGDCCYBQ1LGW
• Metabolomics Workbench ID: 153566
• ChEMBL ID: CHEMBL51085
• Mol file: 60940-34-3.mol

Synonyms:2-phenyl-1,2-benzoisoselenazol-3(2H)-one;2-phenylbenzoisoselenazol-3(2H)-one;DR 3305;DR-3305;DR3305;ebselen;PZ 51;PZ-51;RP 60931;SPI 1005;SPI-1005;SPI1005

Chemical Property of Ebselen

Chemical Property:

• Appearance/Colour: yellow to beige crystalline powder
• Vapor Pressure: 1.07E-06mmHg at 25°C
• Melting Point: 178-181 °C
• Boiling Point: 402.8 °C at 760 mmHg
• PKA: -0.40±0.20(Predicted)
• Flash Point: 197.4 °C
• PSA: 22.00000
• LogP: 2.04770
• Storage Temp.: 2-8°C
• Solubility.: Soluble in ethanol, methanol, acetone, acetonitrile.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 274.98494
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ebselen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T; N; Xi
• Hazard Codes: T,N,Xi
• Statements: 23/25-33-50/53-36/37/38
• Safety Statements: 20/21-28-45-60-61-28A-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C3[Se]2
• Recent ClinicalTrials: SPI-1005 for the Treatment of Meniere's Disease
• Recent EU Clinical Trials: A randomised, parallel group, double blind, placebo controlled, add on clinical trial to investigate whether the lithium mimetic, ebselen, can reduce symptoms of hypomania and mania in bipolar patients experiencing an acute episode of mania or hypomania
• Description: Ebselen is one of the selenium-containing anti-inflammatory drugs.In 2003, Rocha and co-workers identified diselenides as a new class of antiinflammatory agents.In 2014, Nogueira and co-workers reported the synthesis and anti-inflammatory activity of salicyclic-based diselenides and selenocynates.Recently, Wilhelm and co-workers identified 4-phenylselenyl-7-chloroquinoline 270 as a potent antiinflammatory compound.
• Uses: antioxidant, lipoxygenase inhibitor, inhibits oxidation of LDL 2-Phenyl-1,2-benzoselenazol-3-one acts as an antiinfammatory compounds,, in addition to that it acts as a modulator of KVβ subunits. Ebselen is a lipid-soluble organoselenium compound. Numerous in vivo experiments have demonstrated that ebselen is able to inhibit both vasospasm and tissue damage in cerebral stroke/ischemia animal models (i.e. rat, mice, guinea pig and dog).For example, ebselen has been shown to provide significant protection against ischemic damage in both gray and white matter, and in the ventral posterior nucleus of rodent brains.Additionally, administration of ebselen in gerbils significantly reduces neuronal death induced by ischemia and reperfusion in the hippocampal CA1 region.It has been reported that ebselen inhibits inositol monophosphatase and acts as a safe treatment for bipolar disorder. The optimal GPx-like activity of ebselen was observed at neutral or nearphysiological pH (7.4), and the activity of ebselen was barely detected in acidic medium.During ischemia, brain pH falls rapidly within the first 5 min from 7.0 to 6.2, which is not optimal for ebselen's GPx-like activity.Meanwhile, since ebselen has shown promising activity in the treatment of stroke, it seems that GPx-like activity of ebselen in the brain may not occur.Thus, the enzymatic reduction of ebselen by TrxR might be the main contribution to its antioxidant property during ischemia. Unlike inorganic and aliphatic selenium compounds, ebselen does not liberate the selenium moiety, which remains within the ring structure. Subsequent metabolism involves methylation, glucuronidation and hydroxylation. Additionally, ebselen could also inhibit enzymes such as lipoxygenases, nitric oxide synthases, nitrogen oxides, protein kinase C and H1/K1-ATPase. Besides the relationship with redox systems, another neuroprotective mechanism of ebselen is involved in controlling the expression of gaminobutyric acid shunt enzymes to supply the tricarboxylic acid cycle, and significantly inhibiting acetylcholinesterase activity,demonstrating its engagement in the metabolic system.
• Clinical Use: Ebselen and its analogs have also been shown to be inhibitors of Bacillus anthracis TrxR. The ebselen analogs displayed antibacterial activity on Bacillus subtilis, S. aureus, Bacillus cereus and M. tuberculosis. There existed a high resistance barrier for the bacteria to develop ebselen-resistant strains and isolating resistant mutants was found to be difficult and, ultimately, unsuccessful.28 The reason for the difficulty of developing ebselen-resistant bacteria may be because ebselen has exerted a multiple drug-target mechanism, although the exact mechanism is not yet known. In addition to the thioredoxin and GSH systems, ebselen has been reported to have some other potential targets in bacteria, which may help it to overcome the bacterial drug resistance. Ebselen was identified as an inhibitor of diguanylate cyclases by a high-throughput screening in another study by covalent binding to Cys residues.29 This may block the cyclic-di-GMP signaling pathway, regulating biofilm formation, flagella-mediated motility in Pseudomonas aeruginosa, and thus its pathogenesis. Ebselen was identified as an inhibitor of the cysteine protease domain (CPD) in the Clostridium difficile major virulence factor toxin B (TcdB) by another high-throughput screening study. A CPD can bind with one or two ebselen molecules with a covalent modification probably occurring at the active site Cys. The treatment of ebselen blocked the toxic effects of TcdB and the pathology of C. difficile infection in mice.30 Another study also indicated that ebselen is a potent inhibitor of the M. tuberculosis Ag85 complex by binding covalently to a Cys residue (C209) located near the Ag85C active site, which is central to the synthesis of major components of the inner and outer leaflets of the mycobacterial outer membrane.

Technology Process of Ebselen

There total 25 articles about Ebselen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,2‘-diselenobis(N-phenylbenzamide) (106663-84-7) → 2-phenyl-1,2-benzoisoselenazol-3(2H)-one (60940-34-3)

Guidance literature:

With dihydrogen peroxide; In chloroform-d1;

DOI:10.1002/chem.200801258

Reference yield: 100.0%

ebselen seleninic acid (356761-43-8) → 2-phenyl-1,2-benzoisoselenazol-3(2H)-one (60940-34-3)

Guidance literature:

In methanol; acetonitrile; for 24h; Heating;

DOI:10.1002/chem.200801258

Reference yield: 95.0%

2-phenyl-1,2-benzioselenazol-3(2H)-one selenoxide (104473-83-8) → 2-phenyl-1,2-benzoisoselenazol-3(2H)-one (60940-34-3)

Guidance literature:

With thioredoxin reductase; NADPH; In methanol; phosphate buffer; for 0.0666667h; Kinetics;

DOI:10.1021/tx980223r

upstream raw materials:

2-(chloroseleno)benzoyl chloride

aniline

3-chloro-2-phenyl-benzo[d]isoselenazolium; chloride

N-phenyl benzoyl amide

Refernces

• 1、 Cao, Hongxuan,Chen, Han,Han, Xinya,Huang, Yunyuan,Liu, Jiaqi,Peng, Chao,Rao, Li,Ren, Yanliang,Sheng, Chunquan,Su, Chen,Tu, Jie,Wan, Chen,Wan, Jian,Wen, Wuqiang. "Structure-Guided Discovery of the Novel Covalent Allosteric Site and Covalent Inhibitors of Fructose-1,6-Bisphosphate Aldolase to Overcome the Azole Resistance of Candidiasis". . p. 2656 - 2674. Retrieved 2022/02/09.
• 2、 Kim, Soo-Kyoung,Ngo, Huy X.,Dennis, Emily K.,Thamban Chandrika, Nishad,Deshong, Philip,Garneau-Tsodikova, Sylvie,Lee, Vincent T.. "Inhibition of Pseudomonas aeruginosa Alginate Synthesis by Ebselen Oxide and Its Analogues". . p. 1713 - 1726. Retrieved 2021/05/10.