Synthesis, structure and reactivity of [o-(2,6-diisopropylphenyliminomethinyl)phenyl]selenenyl selenocyanate (RSeSeCN) and related derivatives

Rakesh, Prakul; Singh, Harkesh B.; Jasinski, Jerry P.; Golen, James A.

doi:10.1039/c4dt00157e

Cited by 7 publications

(3 citation statements)

References 39 publications

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“…In 2014, Singh and co-workers reported the first example of a stable selenenyl selenocyanate (13) having a Se−Se bond. 19 However, the compound did not exhibit any GPx-like antioxidant activity. In 2020, Frizon et al reported a series of allylic selenocyanates, such as compounds 14−16, and evaluated for their antioxidant activities in cultured mouse neurons under oxidative stress induced by H 2 O 2 .…”

Section: ■ Introductionmentioning

confidence: 94%

“…Interestingly, compound 12 , having a primary amino group, was shown to elevate the level of antioxidant enzymes such as GPx and thioredoxin reductase in normal Swiss albino mice models. In 2014, Singh and co-workers reported the first example of a stable selenenyl selenocyanate ( 13 ) having a Se–Se bond . However, the compound did not exhibit any GPx-like antioxidant activity.…”

Section: Introductionmentioning

confidence: 99%

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Benzimidazole- and Imidazole-Fused Selenazolium and Selenazinium Selenocyanates: Ionic Organoselenium Compounds with Efficient Peroxide Scavenging Activities

et al. 2021

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Three new classes of ionic organoselenium compounds containing cationic benzimidazolium and imidazolium ring systems with selenocyanates as counterions are described. The cyclization of N,N′-disubstituted benzimidazolium and imidazolium bromides having N-(CH2)2-Br and N-(CH2)3-Br groups in the presence of potassium selenocyanate (KSeCN) led to formation of the corresponding selenazolium selenocyanates (21a, 21b, 22a, and 22b) and selenazinium selenocyanates (21c, 21d, 22c, and 22d). However, the open-chain selenocyanates with additional selenocyanate counterions (21e, 21f, 22e, and 22f) were formed from the N,N′-disubstituted benzimidazolium and imidazolium bromides having N-(CH2)6-Br groups. Mechanistic studies were carried out to understand the feasibility of such cyclization processes in the presence of KSeCN. The compounds were studied further for their potencies to catalytically reduce H2O2 in the presence of thiols. Interestingly, the cyclic selenazolium (21a, 21b, 22a, and 22b) and selenazinium compounds (21c, 21d, 22c, and 22d) exhibited significantly higher antioxidant activities than the corresponding acyclic selenocyanates (21f, 22e, and 22f). Selected compounds (22d and 22e) were further evaluated for their potencies in modulating the intracellular level of reactive oxygen species (ROS) in a representative macrophage cell line (RAW 264.7). Owing to the cationic nature of compounds, they may target and scavenge mitochondrial ROS in the cellular medium.

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Section: ■ Introductionmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Benzimidazole- and Imidazole-Fused Selenazolium and Selenazinium Selenocyanates: Ionic Organoselenium Compounds with Efficient Peroxide Scavenging Activities

et al. 2021

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“…Considerable progress has been made recently in the search for simple organoselenium compounds that could mimic the action of the GPx-enzymes. The list of such compounds include ebselen and analogues, diselenides, selenenate/seleninate esters as well as other selenium containing compounds . As assessed by three different methods, the simplest pyridine-derived diselenidedi-2-pyridyl diselenide ( 4a )has been reported to act as a fairly active glutathione peroxidase mimic. ,, Some data are also available concerning the pharmacological properties of this compound .…”

Section: Introductionmentioning

confidence: 99%

Effect of a Bromo Substituent on the Glutathione Peroxidase Activity of a Pyridoxine-like Diselenide

et al. 2015

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In search for better mimics of the glutathione peroxidase enzymes, pyridoxine-like diselenides 6 and 11, carrying a 6-bromo substituent, were prepared. Reaction of 2,6-dibromo-3-pyridinol 5 with sodium diselenide provided 6 via aromatic nucleophilic substitution of the 2-bromo substituent. LiAlH4 caused reduction of all four ester groups and returned 11 after acidic workup. The X-ray structure of 6 showed that the dipyridyl diselenide moiety was kept in an almost planar, transoid conformation. According to NBO-analysis, this was due to weak intramolecular Se···O (1.1 kcal/mol) and Se···N-interactions (2.5 kcal/mol). That the 6-bromo substituent increased the positive charge on selenium was confirmed by NPA-analysis and seen in calculated and observed (77)Se NMR-shifts. Diselenide 6 showed a more than 3-fold higher reactivity than the corresponding des-bromo compound 3a and ebselen when evaluated in the coupled reductase assay. Experiments followed for longer time (2 h) confirmed that diselenide 6 is a better GPx-catalyst than 11. On the basis of (77)Se-NMR experiments, a catalytic mechanism for diselenide 6 was proposed involving selenol, selenosulfide and seleninic acid intermediates. At low concentration (10 μM) where it showed only minimal toxicity, it could scavenge ROS produced by MNC- and PMNC-cells more efficiently than Trolox.

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Transition‐Metal‐Free C−S, C−Se, and C−Te Bond Formation from Organoboron Compounds

Sacramento

Costa

Barcellos

et al. 2021

The Chemical Record

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The present review describes the successful application of organoboron compounds in transition-metal-free CÀ S, CÀ Se, and CÀ Te bond formations. We presented studies regarding these C-Chalcogen bond formations using organoboron reagents, such as boronic acids, boronic esters, borate anions, and several sources of chalcogen atoms/moieties. Moreover, a broad range of transition-metal-free approaches to synthesize sulfides, selenides, and tellurides were described using conventional heating methods, which are sometimes green since they use green solvents, safe reagents, among others. Furthermore, protocols using alternative energy sources, including ultrasound, microwave irradiation, photocatalysis, and electrolytic processes, were also shown to be suitable. These protocols were applied to prepare a broad scope of functionalized chalcogenides with high molecular diversity. These studies and their proposed mechanisms were also reported herein in addition to the reuse of reaction promoters.

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Synthesis, structure and reactivity of [o-(2,6-diisopropylphenyliminomethinyl)phenyl]selenenyl selenocyanate (RSeSeCN) and related derivatives

Cited by 7 publications

References 39 publications

Benzimidazole- and Imidazole-Fused Selenazolium and Selenazinium Selenocyanates: Ionic Organoselenium Compounds with Efficient Peroxide Scavenging Activities

Benzimidazole- and Imidazole-Fused Selenazolium and Selenazinium Selenocyanates: Ionic Organoselenium Compounds with Efficient Peroxide Scavenging Activities

Effect of a Bromo Substituent on the Glutathione Peroxidase Activity of a Pyridoxine-like Diselenide

Transition‐Metal‐Free C−S, C−Se, and C−Te Bond Formation from Organoboron Compounds

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