89780-24-5

Upstream product

• 320774-35-4 2-iodo-N-(pyridine-3-yl)benzamide 
• 462-08-8 pyridin-3-ylamine 
• 609-67-6 2-Iodobenzoyl chloride 
• 88-67-5 2-Iodobenzoic acid 
• 1441-85-6 2-(chloroseleno)benzoyl chloride 

Relevant academic research and scientific papers

The Mpro structure-based modifications of ebselen derivatives for improved antiviral activity against SARS-CoV-2 virus

The main protease (Mpro or 3CLpro) of SARS-CoV-2 virus is a cysteine enzyme critical for viral replication and transcription, thus indicating a potential target for antiviral therapy. A recent repurposing effort has identified ebselen, a multifunctional drug candidate as an inhibitor of Mpro. Our docking of ebselen to the binding pocket of Mpro crystal structure suggests a noncovalent interaction for improvement of potency, antiviral activity and selectivity. To test this hypothesis, we designed and synthesized ebselen derivatives aimed at enhancing their non-covalent bonds within Mpro. The inhibition of Mpro by ebselen derivatives (0.3 μM) was screened in both HPLC and FRET assays. Nine ebselen derivatives (EBs) exhibited stronger inhibitory effect on Mpro with IC50 of 0.07–0.38 μM. Further evaluation of three derivatives showed that EB2-7 exhibited the most potent inhibition of SARS-CoV-2 viral replication with an IC50 value of 4.08 μM in HPAepiC cells, as compared to the prototype ebselen at 24.61 μM. Mechanistically, EB2-7 functions as a noncovalent Mpro inhibitor in LC-MS/MS assay. Taken together, our identification of ebselen derivatives with improved antiviral activity may lead to developmental potential for treatment of COVID-19 and SARS-CoV-2 infection.

Benzisoselenazolone derivative, preparation method and application in anti-coronavirus drugs

The invention belongs to the technical field of anti-coronavirus drug discovery, discloses a benzisoselenazolone derivative, a preparation method and application of the benzisoselenazolone derivativein coronavirus resistance, and relates to synthesis of a

Neuroprotective and anti-neuroinflammatory properties of ebselen derivatives and their potential to inhibit neurodegeneration

Ebselen (EBS) is an organo-selenium-containing compound that has anti-inflammatory, antitumor, and antibacterial properties. EBS is being explored as a possible treatment for reperfusion injury and stroke and is under clinical trials as a mimetic of lithium for the treatment of bipolar disorder [Mota et al. Synapse 2020, 74 (7), 1-6] and noise-induced hearing loss as a result of these actives [Martini et al. J. Psychiatr. Res. 2019, 109, 107-117. Slusarczyk et al. Neural Regener. Res. 2019, 17 (7), 1255-1261. Thangamani et al. PLoS One 2015, 10 (7), e0133877. Kil et al. Lancet 2017, 390 (10098), 969-979]. However, we wanted to characterize derivatives of EBS as neuroprotective, anti-neuroinflammatory, and antioxidant compounds. Recently, we have reported on a new thermal and photoinduced copper-mediated cross-coupling between potassium selenocyanate (KSeCN) and N-substituted ortho-halobenzamides to form ebselen derivatives with increased synthetic efficiency [Thanna et al. J. Org. Chem. 2017, 82 (7), 3844-3854]. Our synthesis allows for the varying of the remote benzene ring with various substituents or replacing that ring with heterocyclic rings such as pyridine, pyrrole, thiophene, etc. In this study, we synthesized seven new heterocyclic EBS derivatives to further diversify our EBS library. These 21 compounds were then evaluated for their neuroprotective properties, with four compounds showing an equal or better neuroprotective profile than EBS. Compounds 5, 9, 23, and 27 showed 73, 86, 80, 84% cell viability, respectively, at a 10 μM concentration. These studies were performed using human neuroblastoma SH-SY5Y cells in an oxygen and glucose deprivation (OGD) model of ischemia. At the same concentration, these compounds significantly inhibited lipopolysaccharide-induced nitric oxide and tumor necrosis factor alpha release from Human microglia clone 3 microglial cells. Compounds 9 and 27 showed significantly increased cell viability (84 and 80%, respectively) for SH-SY5Y cells exposed to microglia-activated media. These compounds showed only mild GPx-like reductive activity, with compounds 2, 7, 12, and 14 (115, 96, 95, and 82%, respectively) showing a higher percent rate of oxidation of NADPH in a coupled reaction assay compared to ebselen. This research highlights several derivatives of ebselen that show improved activity as neuroprotective agents over the parent compound.

SUBSTITUTED ISOSELENAZOLONE ANTI-INFLAMMATORY, ANTI-CANCER, CYTOPROTECTIVE, NEUROPROTECTIVE, AND ANTI-OXIDANT AGENTS

Compounds, compositions, and methods for the treatment of infections, inflammation, cancers, tinnitus, Meniere's disease, hearing loss, or bipolar disorder, or for providing cytoprotection against Clostridium difficile toxins, are disclosed.

Azaanalogues of ebselen as antimicrobial and antiviral agents: Synthesis and properties

The different analogues of ebselen - unsubstituted benzisoselenazol-3(2H)- one (2a) 2-pyridylbenzisoselenazol-3(2H)-ones (2b-h) and 7-azabenzisoselenazol- 3(2H)-ones (3a-j) were designed as new selenium-containing antiviral and antimicrobial agents and synthesized. Some of them were found in the antiviral assay in vitro to be strong inhibitors of cythopatic activity of herpes simplex virus type 1 - HSV-1 (compounds 2a,b,f,h, 3a-j) and encephalomyocarditis virus - EMCV (compounds 2a,h, 3a-f,k,l). The compounds 2a,h and 3a-e,j were found to have an appreciable activity against Gram-positive bacteria (Staphylococcus aureus and Bacillus) in vitro, some of them inhibited growth of pathogenic yeasts (Candida albicans) (3a,b) and filamentous fungi (3a-e,f).

Aromatic and Azaaromatic Diselenides, Benzisoselenazolones and Related Compounds as Immunomodulators Active in Humans: Synthesis and Properties

Convenient syntheses of aryl diselenides 2, 1,2-benzisoselenazol-3(2H)-ones 4 and their 1-oxides 7 are reported.Reductive conversions of these compounds to bis(2-carbamoyl)phenyl diselenides 5 and oxidative cyclization of 5 to 1,2-benzisoselenazol-3(2H)-one 1-oxides 7 as the methods for the synthesis of these compounds are reported.Their ability to induce cytokines, such as TNF and IFN-γ, in human peripheral blood leucocyte cultures is described. - Key Words: 1,2-benzisoselenazol-3(2H)-ones/ Cytokine inducers/ Diselenides/ Interferon-gamma/ Tumor necrosis factor

Benzisoselenazolones and a process for the treatment of inflammatory diseases

The invention relates to new benzisoselenazolones of the general formula I STR1 and a process for the treatment of humans suffering from inflammatory diseases of the rheumatic type.