1239668-62-2

Upstream product

• 394-31-0 2-amino-5-hydroxybenzoic acid 

Downstream Products

• 1239668-63-3 5,5'-dimethoxy-2,2'-(diselanediyl)dibenzoic acid 
• 1381782-06-4 5-acetoxy-2-(chloroseleno)benzoyl chloride 
• 1381782-05-3 5,5'-diacetoxy-(2,2'-diselenobisbenzoic acid) 

Relevant academic research and scientific papers

Selenium containing macrocycles: transformation between Se–N/Se–S/Se–Se bonds

Macrocycles possess potential applications in supramolecular chemistry and biosystems. Thus development of new kinds of macrocycles is of significance. Herein, novel macrocycles containing Se–Se/Se–S bonds were synthesized via transformation between selenium related dynamic covalent bonds. A monomer containing two ebselen moieties was synthesized (M1). The Se–N bonds in M1 were reduced by dithiothreitol, forming Se–S linked dimer (D1). To realize the transformation from Se–S bonds to Se–Se bonds, guest molecules were added as template, triggering the formation of Se–Se linked dimer (D2). The formation of these two new kinds of macrocycles was determined by 1H NMR and 77Se NMR, and the necessity of guest molecules was also confirmed. The introduction of ebselen moieties and Se–S bonds or Se–Se bonds into macrocycles may endow it with new responsiveness and bioactivities, as well as new types of host-guest chemistry.

Computer-assisted designed "selenoxy-chinolin": A new catalytic mechanism of the GPx-like cycle and inhibition of metal-free and metal-associated Aβ aggregation

Using support from rational computer-assisted design, a novel series of hybrids (selenoxy-chinolin) designed by fusing the metal-chelating agent CQ and the antioxidant ebselen were synthesized and evaluated as multitarget-directed ligands. Most of the hybrids demonstrated significant ability to mimic GPx, which is highly consistent with the prediction results of DFT studies for the selenenyl sulfide intermediates in the computational design. Using 77Se, 1H and 13C NMR spectroscopy and high-resolution mass spectroscopy (HRMS), a novel catalytic mechanism, including a new selenium quinone active species, was first demonstrated. 2D NMR studies indicated that the typical hybrid has an effective interaction with Aβ. In addition, the optimal compound 12k was found to possess an excellent ability to scavenge peroxide and to inhibit self- and metal-induced Aβ aggregation, and an ability to disassemble preformed self- and metal-induced Aβ aggregates effectively. Furthermore, 12k was able to penetrate the central nervous system (CNS) and did not exhibit any acute toxicity in mice at doses up to 2000 mg kg-1. Overall, we demonstrated that hybrid 12k, through rational structure-based computational design, shows a potential for development as a therapeutic agent in AD.

Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy

Thioredoxin reductase (TrxR) is critical for cellular redox regulation and is involved in tumor proliferation, apoptosis and metastasis. Its C-terminal redox-active center contains a cysteine (Cys497) and a unique selenocysteine (Sec498), which are exposed to solvent and easily accessible. Thus, it is becoming an important target for anticancer drugs. Selective inhibition of TrxR by 1,2-(bis-1,2-benzisoselenazol-3(2H)-one)ethane (4a) prevents proliferation of several cancer cell lines both in vivo and in vitro. Using the structure of 4a as a starting point, a series of novel bis-1,2-benzisoselenazol-3(2H)-ones was designed, prepared and tested to explore the structure-activity relationships (SARs) for this class of inhibitor and to improve their potency. Notably, 1,2-(5,5′-dimethoxybis(1,2-benzisoselenazol-3(2H)-one))ethane (12) was found to be more potent than 4a in both in vitro and in vivo evaluation. Its binding sites were confirmed by biotin-conjugated iodoacetamide assay and a SAR model was generated to guide further structural modification.