60940-33-2

Basic information

• Product Name: 2-benzylbenzo[d][1,2]selenazol-3(2H)-one
• Synonyms: 2-benzylbenzo[d][1,2]selenazol-3(2H)-one
• CAS NO: 60940-33-2
• Molecular Weight: 288.207
• Mol File: 60940-33-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 2-benzylbenzo[d][1,2]selenazol-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzylbenzo[d][1,2]selenazol-3(2H)-one(60940-33-2)
• EPA Substance Registry System: 2-benzylbenzo[d][1,2]selenazol-3(2H)-one(60940-33-2)

Safety Data

• Hazardous Substances Data: 60940-33-2(Hazardous Substances Data)

Upstream product

• 2099-63-0 anthranilic acid hydrochloride 
• 134-20-3 2-carbomethoxyaniline 
• 98-88-4 benzoyl chloride 
• 100-46-9 benzylamine 
• 1485-70-7 N-benzylbenzamide 
• 609-67-6 2-Iodobenzoyl chloride 
• 7782-49-2 selenium 
• 7506-50-5 N-(o-chlorobenzoyl)benzylamine 
• 118-92-3 anthranilic acid 
• 6512-83-0 2,2'-diselanediyl-di-benzoic acid 
• 82082-50-6 N-benzyl-2-bromobenzamide 
• 73178-23-1 N-benzyl-2-iodobenzamide 
• 3811-73-2 2-mercaptopyridine-1-oxide sodium salt 
• 1441-85-6 2-(chloroseleno)benzoyl chloride 

Downstream Products

• 60940-55-8 2-benzyl-3-chloro-benzo[d]isoselenazolium; chloride 
• 101563-10-4 S-(2-Benzylcarbamoyl-phenylselenyl)-L-cysteinethylester 
• 60940-40-1 benzo[d]isoselenazol-3-yl-benzyl-amine 
• 106663-70-1 bis[2-(benzylcarbamoyl)phenyl] diselenide 
• 114744-70-6 S-(2-benzyl carbamoyl benzeneselenenyl)benzylmercaptan 
• 104473-79-2 2-benzyl-1,2-benzisoselenazol-3(2H)-one-Se-oxide 
• 60940-34-3 2-phenyl-1,2-benzoisoselenazol-3(2H)-one 
• 101563-08-0 S-(2-benzylcarbamoyl-phenylselenyl)-D-penicillamine 

Relevant articles and documents

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

Inhibition of Pseudomonas aeruginosa Alginate Synthesis by Ebselen Oxide and Its Analogues

Pseudomonas aeruginosa is a Gram-negative opportunistic pathogen that is frequently found in the airways of cystic fibrosis (CF) patients due to the dehydrated mucus that collapses the underlying cilia and prevents mucociliary clearance. During this life-long chronic infection, P. aeruginosa cell accumulates mutations that lead to inactivation of the mucA gene that results in the constitutive expression of algD-algA operon and the production of alginate exopolysaccharide. The viscous alginate polysaccharide further occludes the airways of CF patients and serves as a protective matrix to shield P. aeruginosa from host immune cells and antibiotic therapy. Development of inhibitors of alginate production by P. aeruginosa would reduce the negative impact from this viscous polysaccharide. In addition to transcriptional regulation, alginate biosynthesis requires allosteric activation by bis (3′-5′)-cyclic dimeric guanosine monophosphate (c-di-GMP) binding to an Alg44 protein. Previously, we found that ebselen (Eb) and ebselen oxide (EbO) inhibited diguanylate cyclase from synthesizing c-di-GMP. In this study, we show that EbO, Eb, ebsulfur (EbS), and their analogues inhibit alginate production. Eb and EbS can covalently modify the cysteine 98 (C98) residue of Alg44 and prevent its ability to bind c-di-GMP. However, P. aeruginosa with Alg44 C98 substituted with alanine or serine was still inhibited for alginate production by Eb and EbS. Our results indicate that EbO, Eb, and EbS are lead compounds for reducing alginate production by P. aeruginosa. Future development of these inhibitors could provide a potential treatment for CF patients infected with mucoid P. aeruginosa.

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.