153871-75-1

Usage

InChI:InChI=1/C14H9NO3Se/c16-13-11-3-1-2-4-12(11)19-15(13)10-7-5-9(6-8-10)14(17)18/h1-8H,(H,17,18)

Upstream product

• 134-20-3 2-carbomethoxyaniline 
• 94-09-7 p-aminoethylbenzoate 
• 81743-93-3 ethyl 4-(3-oxobenzo[d][1,2]selenazol-2(3H)-yl)benzoate 
• 1441-85-6 2-(chloroseleno)benzoyl chloride 
• 6512-83-0 2,2'-diselanediyl-di-benzoic acid 
• 118-92-3 anthranilic acid 
• 609-67-6 2-Iodobenzoyl chloride 
• 310453-98-6 methyl 4-(2-iodobenzamido)benzoate 
• 88-67-5 2-Iodobenzoic acid 
• 150-13-0 4-amino-benzoic acid 

Downstream Products

• 1432022-22-4 (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-(3-oxo-1,2-benzisoselenazol-2(3H)-yl)benzoate 
• 1432022-23-5 (2,3,6,2',3',4',6'-hepta-O-acetyl-β-D-lactosyl)-4-(3-oxo-1,2-benzisoselenazol-2(3H)-yl) benzoate 

Relevant academic research and scientific papers

Synthesis of organoselenium-modified β-cyclodextrins possessing a 1,2-benzisoselenazol-3(2H)-one moiety and their enzyme-mimic study

Six novel H2O-soluble β-cyclodextrin derivatives containing a 1,2-benzisoselenazol-3(2H)-one moiety were synthesized by a convenient method in 25-60% yield and characterized by MS, elemental analysis, IR, 1H-NMR, and UV/VIS spectrosc

Synthesis of a Hybrid between SOD Mimetic and Ebselen to Target Oxidative Stress

Oxidative stress emerged as target in drug discovery due to its diverse role in various diseases, such as cardiovascular, neurodegenerative, and autoimmune diseases. During the last decades, considerable progress was made in the development of compounds with the ability to reduce reactive oxygen species (ROS) like superoxide. However, the dismutation of the latter leads to formation of another harmful ROS, hydrogen peroxide, which can be depleted through peroxidase activity. The present work describes the synthesis of a hybrid, which unifies a superoxide dismutase mimetic, MnIIpyane, and a glutathione peroxidase mimetic, ebselen, that are connected via an amide bond. This unique hybrid is designed in order to convert superoxide into oxygen and water, i.e. as a potential biological agent for complete ROS removal and will be used in the future as mechanistic molecular tool for further elucidation of (patho) physiological consequences of ROS removal.

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

Fructose-1,6-bisphosphate aldolase (FBA) represents an attractive new antifungal target. Here, we employed a structure-based optimization strategy to discover a novel covalent binding site (C292 site) and the first-in-class covalent allosteric inhibitors

1,2-BENZISOSELENAZOL-3(2H)-ONE AND 1,2-BENZISOTHIAZOL-3(2H)-ONE DERIVATIVES AS BETA-LACTAM ANTIBIOTIC ADJUVANTS

Provided herein are compositions and methods useful in the treatment of beta-lactam antibiotic resistant bacteria.

Investigation of synergistic antimicrobial effects of the drug combinations of meropenem and 1,2-benzisoselenazol-3(2H)-one derivatives on carbapenem-resistant Enterobacteriaceae producing NDM-1

The worldwide prevalence of NDM-1-producing bacteria has drastically undermined the clinical efficacy of the last line antibiotic of carbapenems, prompting a need to devise effective strategy to preserve their clinical value. Our previous studies have shown that ebselen can restore the efficacy of meropenem against a laboratory strain that produces NDM-1. Here we report the construction of a focused compound library of 1,2-benzisoselenazol-3(2H)-one derivatives which comprise a total of forty-six candidate compounds. The structure-activity relationship of these compounds and their potential to serve as an adjuvant to enhance the antimicrobial efficacy of meropenem against a collection of clinical NDM-1-producing carbapenem-resistant Enterobacteriaceae isolates was examined. Drug combination assays indicated that these derivatives exhibited synergistic antimicrobial activity when used along with meropenem, effectively restoring the activity of carbapenems against the resistant strains tested in a Galleria mellonella larvae in vivo infection model. The mode of inhibition of one compound, namely 11_a38, which was depicted when tested on the purified NDM-1 enzyme, indicated that it could covalently bind to the enzyme and displaced one zinc ion from the active site. Overall, this study provides a novel 1,2-benzisoselenazol-3(2H)-one scaffold that exhibits strong synergistic antimicrobial activity with carbapenems, and low cytotoxicity. The prospect of application of such compounds as carbapenem adjuvants warrants further evaluation.

Design, synthesis, and biological evaluation of histone deacetylase inhibitors possessing glutathione peroxidase-like and antioxidant activities against Alzheimer's disease

A series of hybrids containing the pharmacophores of the histone deacetylase (HDAC) inhibitor, SAHA, and the antioxidant ebselen were designed and synthesized as multi-target-directed ligands against Alzheimer's disease. An in vitro assay indicated that some of these molecules exhibit potent HDAC inhibitory activity and ebselen-related pharmacological effects. Specifically, the optimal compound 7f was found to be a potent HDAC inhibitor (IC50 = 0.037 μM), possessing rapid hydrogen peroxide scavenging activity and glutathione peroxidase-like activity (ν0 = 150.0 μM min?1) and good free oxygen radical absorbance capacity (value of ORAC: 2.2). Furthermore, compound 7f showed significant protective effects against damage induced by H2O2 and the ability to prevent ROS accumulation in PC12 cells.

Evaluation of substituted ebselen derivatives as potential trypanocidal agents

Human African trypanosomiasis is a disease of sub-Saharan Africa, where millions are at risk for the illness. The disease, commonly referred to as African sleeping sickness, is caused by an infection by the eukaryotic pathogen, Trypanosoma brucei. Previously, a target-based high throughput screen revealed ebselen (EbSe), and its sulfur analog, EbS, to be potent in vitro inhibitors of the T. brucei hexokinase 1 (TbHK1). These molecules also exhibited potent trypanocidal activity in vivo. In this manuscript, we synthesized a series of sixteen EbSe and EbS derivatives bearing electron-withdrawing carboxylic acid and methyl ester functional groups, and evaluated the influence of these substituents on the biological efficacy of the parent scaffold. With the exception of one methyl ester derivative, these modifications ablated or blunted the potent TbHK1 inhibition of the parent scaffold. Nonetheless, a few of the methyl ester derivatives still exhibited trypanocidal effects with single-digit micromolar or high nanomolar EC50values.

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