Rongalite®/PEG-400 as reducing system in the synthesis of new glycerol-derived selenol esters using anhydrides and bis-(2,2-dimethyl-1,3-dioxolanylmethyl)diselenide as substrates

Perin, Gelson; Silveira, Marilice B.; Barcellos, Angelita M.; Araujo, Daniela R.; Jacob, Raquel G.; Barcellos, Thiago; Lenardão, Eder J.

doi:10.3998/ark.5550190.p009.746

Cited by 5 publications

(2 citation statements)

References 46 publications

(53 reference statements)

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“…CFA (Santa Cruz Biotech., EUA) and all other chemicals used were of analytical grade and obtained from Sigma-Aldrich, (St. Louis, MO). Se-DMC (Figure ) was prepared and characterized in our laboratory using the method of Perin et al Evaluation of the mass spectrometer (MS), hydrogen nuclear magnetic resonance spectra ( 1 H NMR), carbon-13 nuclear magnetic resonance spectra ( 13 C-NMR), and high-resolution mass spectra (HRMS) presented analytical and spectroscopic data in full agreement with the Se-DMC assigned structure. Vehicles of meloxicam and Se-DMC were an isotonic saline solution and canola oil, respectively.…”

Section: Methodsmentioning

confidence: 99%

Se-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl] 4-Chlorobenzoselenolate Attenuates Inflammatory Response, Nociception, and Affective Disorders Related to Rheumatoid Arthritis in Mice

Wilhelm

Soares

Reis

et al. 2021

ACS Chem. Neurosci.

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Despite major advances, not all patients achieve rheumatoid arthritis (RA) remission, thus highlighting a pressing need for new therapeutic treatments. Given this scenario, this study sought to evaluate Se-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl] 4chlorobenzoselenolate (Se-DMC) potential on a complete Freund's adjuvant (CFA)-induced unilateral arthritis model. The effects of Se-DMC (5 mg/kg; oral dose) and meloxicam (5 mg/kg; oral dose), both administered to animals daily for 14 days, on paw edema, mechanical sensitivity, neurobehavioral deficits (anxiogenic-and depressive-like behaviors), Na + /K + -ATPase activity, oxidative stress, and inflammation were evaluated in male Swiss mice exposed to CFA (intraplantar injection of 0.1 mL; 10 mg/ mL). Se-DMC reduced the paw withdrawal threshold and CFA-induced paw edema. Histopathological results revealed the antiedematogenic potential of the compound, which was evidenced by lower quantities of dilated lymphatic vessels compared with the CFA group. Se-DMC reduced mRNA relative expression levels of tumor necrosis factor-α (TNF-α) and nuclear factor-κB (NF-κB) in the hippocampus and paw of CFA mice. The CFA-induced anxiogenic-and depressive-like behaviors were reversed by Se-DMC to the control levels in the elevated plus-maze and tail suspension tests. Se-DMC reduced the paw reactive species levels and restored the superoxide dismutase (hippocampus and paw) and Na + /K + -ATPase (hippocampus) activities previously increased by CFA. Moreover, CFA administration inhibited serum creatinine kinase activity, albeit the Se-DMC effects did not appear to involve the modulation of this enzyme and were equal to or greater than meloxicam. Se-DMC attenuates CFA-induced inflammatory response, nociception, and neurobehavioral deficits in mice.

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Section: Methodsmentioning

confidence: 99%

Se-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl] 4-Chlorobenzoselenolate Attenuates Inflammatory Response, Nociception, and Affective Disorders Related to Rheumatoid Arthritis in Mice

Wilhelm

Soares

Reis

et al. 2021

ACS Chem. Neurosci.

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“…In 2017, Lenardão reported the synthesis of selenol esters from diselenide under the reduction of rongalite (Scheme 22). [27] In this process, firstly, in the presence of K 2 CO 3 , rongalite decomposes to produce HSO 2 anion, which can participate in the single electron reduction of diselenide to generate selenium radial 22-A and selenium anion 22-B. Selenium radial Scheme 22 Synthesis of selenol esters from diselenide by Lenardão's group 22-A can be further reduced to selenium anion 22-B.…”

Section: Rongalite As a Single Electron Donor Or Reductantmentioning

confidence: 99%

Rongalite as a Versatile Reagent in Organic Synthesis^†

Wang,

Chen,

et al. 2023

Chin. J. Chem.

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Comprehensive SummaryThis review provides a comprehensive summary of progress to date in the utilization of rongalite as a versatile reagent in organic synthesis, with a focus on recent research. The contents have been organized according to the functions exhibited by rongalite. Reaction mechanisms are provided, demonstrating the multifaceted roles of this compound in various transformations, including as a sulfone, C1 or masked proton source and as a single electron donor or reducing agent.This article is protected by copyright. All rights reserved.

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Synthesis of Selenium Derivatives using Organic Selenocyanates as Masked Selenols: Chemical Reduction with Rongalite as a Simpler Tool to give Nucleophilic Selenides

Castro‐Godoy,

Heredia,

Bouchet

et al. 2024

ChemPlusChem

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The chemical reduction within a family of organic selenocyanates, as masked selenols, using reducing agents, such as Rongalite, sodium dithionite, and sodium thiosulfate is investigated. Using Rongalite, the corresponding diselenides were obtained quantitatively and selectively in very good to excellent yields (51‐100%) starting from alkyl, aryl, and benzyl selenocyanates. The scope of the reaction is unaffected by the electronic nature of the substituents. Furthermore, the reducing agent, Rongalite, is compatible with hydrolysable and reducing‐sensitive functional groups. Additionally, a simple methodology employing the in‐situ generated benzyl selenolate anion (PhCH2Se‾) to promote aliphatic nucleophilic substitution, epoxide ring opening, and Michael addition reactions has been developed; thus extending the structural diversity of the synthesized selenium derivatives.

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Rongalite®/PEG-400 as reducing system in the synthesis of new glycerol-derived selenol esters using anhydrides and bis-(2,2-dimethyl-1,3-dioxolanylmethyl)diselenide as substrates

Cited by 5 publications

References 46 publications

Se-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl] 4-Chlorobenzoselenolate Attenuates Inflammatory Response, Nociception, and Affective Disorders Related to Rheumatoid Arthritis in Mice

Se-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl] 4-Chlorobenzoselenolate Attenuates Inflammatory Response, Nociception, and Affective Disorders Related to Rheumatoid Arthritis in Mice

Rongalite as a Versatile Reagent in Organic Synthesis^†

Synthesis of Selenium Derivatives using Organic Selenocyanates as Masked Selenols: Chemical Reduction with Rongalite as a Simpler Tool to give Nucleophilic Selenides

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Rongalite®/PEG-400 as reducing system in the synthesis of new glycerol-derived selenol esters using anhydrides and bis-(2,2-dimethyl-1,3-dioxolanylmethyl)diselenide as substrates

Cited by 5 publications

References 46 publications

Se-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl] 4-Chlorobenzoselenolate Attenuates Inflammatory Response, Nociception, and Affective Disorders Related to Rheumatoid Arthritis in Mice

Se-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl] 4-Chlorobenzoselenolate Attenuates Inflammatory Response, Nociception, and Affective Disorders Related to Rheumatoid Arthritis in Mice

Rongalite as a Versatile Reagent in Organic Synthesis†

Synthesis of Selenium Derivatives using Organic Selenocyanates as Masked Selenols: Chemical Reduction with Rongalite as a Simpler Tool to give Nucleophilic Selenides

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Product

Resources

About

Rongalite as a Versatile Reagent in Organic Synthesis^†