106664-01-1

Basic information

• Product Name: 2-(2-methoxyphenyl)benzo[d][1,2]selenazol-3(2H)-one
• Synonyms: 2-(2-methoxyphenyl)benzo[d][1,2]selenazol-3(2H)-one
• CAS NO: 106664-01-1
• Molecular Weight: 304.207
• Mol File: 106664-01-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(2-methoxyphenyl)benzo[d][1,2]selenazol-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-methoxyphenyl)benzo[d][1,2]selenazol-3(2H)-one(106664-01-1)
• EPA Substance Registry System: 2-(2-methoxyphenyl)benzo[d][1,2]selenazol-3(2H)-one(106664-01-1)

Safety Data

• Hazardous Substances Data: 106664-01-1(Hazardous Substances Data)

Upstream product

• 2099-63-0 anthranilic acid hydrochloride 
• 1441-85-6 2-(chloroseleno)benzoyl chloride 
• 90-04-0 2-methoxy-phenylamine 
• 6512-83-0 2,2'-diselanediyl-di-benzoic acid 
• 118-92-3 anthranilic acid 
• 36684-47-6 2-iodo-N-(2-methoxy-phenyl)-benzamide 

Relevant articles and documents

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.

Copper catalyzed/mediated synthetic methodology for ebselen and related isoselenazolones

Scope of the copper catalyzed/mediated selenium-nitrogen coupling reaction has been studied for the synthesis of isoselenazolones. It is noticed that the 2-chloro, 2-bromo-, and 2-iodo-aryl amides substrates can be exploited in the selenium-nitrogen coupling reaction by employing 25-100 mol % of CuI/1,10-phenanthroline (L) and potassium carbonate as a base in DMF. Furthermore, electron rich 2-chloro-arylamides also underwent selenium-nitrogen coupling reaction to give biologically important selenium-nitrogen heterocycles. Also, copper-catalyzed selenium-nitrogen coupling reaction has been meticulously applied for the synthesis of diaryl diselenides having methoxy, amine, and amide functionality from respective aryl iodides in the presence of stoichiometric amount of succinimide as an external Se-N coupling partner.