35350-43-7Relevant articles and documents
Catalytic antioxidant activity of bis-aniline-derived diselenides as GPx mimics
Barbosa, Flavio A. R.,Bettanin, Luana,Botteselle, Giancarlo V.,Braga, Antonio L.,Canto, R?mulo F. S.,Ciancaleoni, Gianluca,Domingos, Josiel B.,Elias, Welman C.,Gallardo, Hugo,Rafique, Jamal,Saba, Sumbal,Salin, Drielly N. O.
supporting information, (2021/08/06)
Herein, we describe a simple and efficient route to access aniline-derived diselenides and evaluate their antioxidant/GPx-mimetic properties. The diselenides were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These diselenides present GPx-mimetic properties, showing better antioxidant activity than the standard GPx-mimetic compounds, ebselen and diphenyl diselenide. DFT analysis demonstrated that the electronic properties of the substituents determine the charge delocalization and the partial charge on selenium, which correlate with the catalytic performances. The amino group concurs in the stabilization of the selenolate intermediate through a hydrogen bond with the selenium.
Naphthalimide derivative containing selenoheterocycle, and preparation method and antiviral application thereof (by machine translation)
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Paragraph 0022; 0053, (2020/07/12)
The invention discloses a selenoheterocycle-containing naphthalimide derivative and a preparation method and an antiviral application thereof, wherein the naphthalimide derivative is 1. H, 3H-selenium xanthene [2, 1, 9 -]Def] Isoquinoline -1, 3 (2)HThe diketone derivative hydrochloride has a structural formula shown in the formula (1 - 7) as shown in the specification. The compound 1 - 7 disclosed by the invention is used for inducing a human host cell II type serine protease TMPMPMPRSS2 promoter region to be rich in guanine DNA sequences to induce formation G - four-chain bodies. The conjugated mother ring structure in compound 1 - 7 can interact with G - four split formed in the research target in π -pi stacking mode through computer molecule simulation experiment, and the side chain can be well combined with the groove structure G - four-chain body. The invention plays an important role in developing clinical medicine development of the naphthalimide derivative containing the selenium heterocycle, and especially has an important value for finding a new antiviral small molecule medicine. (by machine translation)
Mechanistic Studies on the Anodic Functionalization of Alkenes Catalyzed by Diselenides
Wilken, Mona,Ortgies, Stefan,Breder, Alexander,Siewert, Inke
, p. 10901 - 10912 (2018/11/02)
Herein, we present a detailed kinetic and thermodynamic analysis of the anodic allylic esterification of alkenes as well as the bulk application of the anodic amination and esterification of nonactivated alkenes catalyzed by diselenides. The electrochemical study led to a comprehensive picture of the coupled electrochemical and chemical reaction steps. Cyclic voltammetry measurements are consistent with a bimolecular step after initial electrochemical 1e- oxidation of the diphenyl diselenide catalyst, 1a, and therefore we postulate a dimerization of the cation, which reacts very rapidly with the alkene, forming the addition product, i.e. the selenolactone 2a. Subsequent electrochemical oxidation of 2a occurs at a slightly higher potential than initial oxidation of 1a. The second oxidation is also followed by a bimolecular process and we hypothesize a dimerization of the cation, which finally eliminates 1a and protons in the rate-determining step, forming the product. Electrochemical analysis of various catalysts, i.e. nonsterically demanding diaryl diselenides with electron withdrawing and donating substituents, revealed that the oxidation potential of the catalyst and the intermediate can be readily tuned by the substituents, thus, prospectively allowing for a wide application of olefinic and nucleophilic substrates. The substituent pattern at the alkene has a smaller influence on the redox potential of the adduct. Controlled potential electrolysis experiments employing different nucleophiles proved that the reaction can be run electrochemically. The functionalization of unactivated alkenes with N- and O-nucleophiles was successfully demonstrated in several bulk electrolysis experiments, and the products were isolated in good yields.
Selenols are resistant to irreversible modification by HNO
Bianco, Christopher L.,Moore, Cathy D.,Fukuto, Jon M.,Toscano, John P.
, p. 71 - 78 (2016/08/09)
The discovery of nitric oxide (NO) as an endogenously generated signaling species in mammalian cells has spawned a vast interest in the study of the chemical biology of nitrogen oxides. Of these, nitroxyl (azanone, HNO) has gained much attention for its potential role as a therapeutic for cardiovascular disease. Known targets of HNO include hemes/heme proteins and thiols/thiol-containing proteins. Recently, due to their roles in redox signaling and cellular defense, selenols and selenoproteins have also been speculated to be additional potential targets of HNO. Indeed, as determined in the current work, selenols are targeted by HNO. Such reactions appear to result only in formation of diselenide products, which can be easily reverted back to the free selenol. This characteristic is distinct from the reaction of HNO with thiols/thiolproteins. These findings suggest that, unlike thiolproteins, selenoproteins are resistant to irreversible oxidative modification, support that Nature may have chosen to use selenium instead of sulfur in certain biological systems for its enhanced resistance to electrophilic and oxidative modification.
Compound for treatment or prevention of breast cancer
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Paragraph 0059; 0060; 0063, (2018/02/04)
The invention discloses a compound for treatment or prevention of breast cancer, specifically a 2-phenyl benzoselenazole compound, its pharmaceutically acceptable salt and easily hydrolysable prodrug. The invention further discloses a pharmaceutical composition containing the compounds and use of the compound in preparation of drugs for treatment or prevention of breast cancer in mammals. The compound involved in the invention can effectively inhibit or reduce mammalian breast cancer cell growth or proliferation, at the same time, the compound has no inhibiting effect on the growth of partial test cells except for breast cancer cells and has good selectivity. The compound shows more obvious efficacy, high selectivity, low toxicity and small side effect. (formula of the compound).
Aldehyde capture ligation for synthesis of native peptide bonds
Raj, Monika,Wu, Huabin,Blosser, Sarah L.,Vittoria, Marc A.,Arora, Paramjit S.
supporting information, p. 6932 - 6940 (2015/06/16)
Chemoselective reactions for amide bond formation have transformed the ability to access synthetic proteins and other bioconjugates through ligation of fragments. In these ligations, amide bond formation is accelerated by transient enforcement of an intramolecular reaction between the carboxyl and the amine termini of two fragments. Building on this principle, we introduce an aldehyde capture ligation that parlays the high chemoselective reactivity of aldehydes and amines to enforce amide bond formation between amino acid residues and peptides that are difficult to ligate by existing technologies.
Synthesis of disulfides and diselenides by copper-catalyzed coupling reactions in water
Li, Zhengkai,Ke, Fang,Deng, Hang,Xu, Hualong,Xiang, Haifeng,Zhou, Xiangge
supporting information, p. 2943 - 2946 (2013/07/25)
A simple and efficient protocol for copper-catalyzed coupling reactions between aryl halides and elemental sulfur or selenium has been developed. A variety of disulfides and diselenides can be obtained in moderate to excellent yields up to 96%. The Royal Society of Chemistry 2013.
Sensitive near-infrared fluorescent probes for thiols based on Se-N bond cleavage: Imaging in living cells and tissues
Wang, Rui,Chen, Lingxin,Liu, Ping,Wang, Yunqing,Zhang, Qin
supporting information, p. 11343 - 11349,7 (2012/12/12)
Cy-NiSe and Cy-TfSe were designed and synthesized as sensitive near-infrared (NIR) fluorescent probes for detecting thiols on the basis of Se-N bond cleavage both in cells and in tissues. Since a donor-excited photoinduced electron transfer (d-PET) process occurs between the modulator and the fluorophore, Cy-NiSe and Cy-TfSe have weak fluorescence. On titration with glutathione, the free dye exhibits significant fluorescence enhancement. The two probes are sensitive and selective for thiols over other relevant biological species. They can function rapidly at pH 7.4, and their emission lies in the NIR region. Confocal imaging confirms that Cy-NiSe and Cy-TfSe can be used for detecting thiols in living cells and tissues. Turn-on fluorescent probes Cy-NiSe and Cy-TfSe, which show weak fluorescence due to donor-excited photoinduced electron transfer, release near-infrared fluorescent dye Cy7-MeAm on cleavage of the Se-N bond by thiols. Thus, they can be used for real-time imaging of thiols such as glutathione in living cells and tissue (see figure). Copyright
Bis(2-aminophenyl) diselenide derivatives with amino acids moieties as potential antivirals and antimicrobials
Dbrowska, Ewa,Ptka-Ottlik, Magdalena,Palus, Jerzy
experimental part, p. 1082 - 1086 (2009/04/10)
The seleno-organic compounds based on bis(2-aminophenyl) diselenide-1 are potential antiviral, antibacterial and antifungal agents.1 In this work, we reported synthesis of bis(2-aminophenyl) diselenide derivatives 2, 3 having amino acid and dipeptide moieties. This process was realized by acylation of amine groups in 1 with N-blocked amino acids, using the active esters method (with DCC and HOBT). After removing protective groups successive N-blocked amino acids were added the same way as previously. All compounds have been tested against broad spectrum of pathogenic microorganisms (Staphylococcus aureus, Staphylococcus simulans, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Candida albicans, Aspergillus niger) and viruses (HSV-1, EMCV, VSV), in vitro. Most of them exhibited high activity against EMCV. Some of tested compounds were active against gram-positive bacteria species (Staphylococcus aureus, Staphylococcus simulans) and yeast Candida albicans.
Functionalized alkyl and aryl diselenides as antimicrobial and antiviral agents: Synthesis and properties
Wojtowicz,Chojnacka,Mlochowski,Palus,Syper,Hudecova,Uher,Piasecki,Rybka
, p. 1235 - 1242 (2007/10/03)
The different dialkyl and diaryl diselenides with carbamoyl and sulfamoyl moieties 2, 3, 5 and other substituents in the ortho position of benzene ring 4, 7, 8 as well as derivatives of 1,2,4-benzoselenadiazine (6) were designed as antiviral and antimicrobial agents and synthesized. Some of them, particularly 8a and 8b, were found in the antiviral assay in vitro to be strong inhibitors of cytopathic activity encephalomyocarditis virus (EMCV). The compound 4a and 8a were found to have a broad spectrum of acivity against bacteria, yeasts and pathogenic fungi in vitro.
