A Facile Method for β‐Selenoglycoside Synthesis Using β‐p‐Methylbenzoyl Selenoglycoside as the Selenating Unit.

Kawai, Yumiko; Ando, Hiromune; Ozeki, Hideya; Koketsu, Mamoru; Ishihara, Hideharu

doi:10.1002/chin.200609202

Cited by 2 publications

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“…BMD (Figure ) was prepared and characterized in our laboratory by the method previously described Kawai et al . Analysis of the 1 H NMR and 13 C NMR spectra showed analytical and spectroscopic data in full agreement with their assigned structures.…”

Section: Methodsmentioning

confidence: 88%

Hepatoprotective effect of bis(4‐methylbenzoyl) diselenide against CCl₄‐induced oxidative damage in mice

Filho

Fabbro

Boeira

et al. 2012

Cell Biochemistry & Function

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From a pharmacological point of view, organoseleniums are compounds with important and interesting antioxidant and biological activities. The aim of this study was to evaluate the hepatoprotective effect of bis(4-methylbenzoyl) diselenide (BMD) against carbon tetrachloride (CCl4 )-induced oxidative damage in mice. The animals received BMD (25 mg/kg p.o., for 3 days), and after 1 day, CCl4 (1 mg/kg body weight) was administered by intraperitoneal route. One day after the CCl4 exposure, the animals were euthanized for biochemical and histological analysis. Treatment with BMD (25 mg/kg p.o.) protected against aspartate aminotransferase, alanine aminotransferase, alkaline phosphatase, gamma-glutamyl transferase and lactate dehydrogenase activity increases induced by CCl4 plasma exposure. Treatment with BMD (25 mg/kg) protected against increases in thiobarbituric reactive species and decreasing non-protein thiols and ascorbic acid levels in liver of mice. Catalase and superoxide dismutase activity inhibition in the liver caused by CCl4 were protected by treatment with BMD (25 mg/kg). Glutathione S-transferase activity was inhibited by CCl4 and remained unaltered even after treatment with BMD. Sections of liver from CCl4 -exposed mice presented an intense infiltration of inflammatory cells and loss of the cellular architecture. BMD (25 mg/kg) attenuated CCl4 -induced hepatic histological alterations. The results demonstrated the hepatoprotective effects of BMD in the mouse liver, possibly by modulating the antioxidant status.

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Section: Methodsmentioning

confidence: 88%

Hepatoprotective effect of bis(4‐methylbenzoyl) diselenide against CCl₄‐induced oxidative damage in mice

Filho

Fabbro

Boeira

et al. 2012

Cell Biochemistry & Function

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“…The above results revealed that the yields of the product dropped with the decrease in basicity. Further, these findings suggested that acyl thioglycoside is effectively activated by using 1.5 equiv of Cs 2 CO 3 and readily produces the thiolate anion in situ (according to the methods of Ando and Ishihira 23 ), which completely converted under optimized reaction conditions to thioglycoside 4a in 97% yield (entry 2). With these encouraging results, we endeavor to afford Seglycoside 5a by employing galactosylselenoacetate 3a, coupled with p-QM 1a under the same optimized conditions.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Atom-Economic Synthesis of Unsymmetrical gem-Diarylmethylthio/Seleno Glycosides via Base Mediated C(O)–S/Se Bond Cleavage and Acyl Transfer Approach of Glycosylthio/Selenoacetates

Azeem

Mandal

2023

J. Org. Chem.

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Herein, we invented the Cs2CO3-mediated atom economic method that streamlines the scission of the C(O)–S/Se bond involving the in situ generation of an anomeric thiolate/selenolate anion, which reacted with p-QMs to yield novel unsymmetrical gem-diarylmethylthio/seleno glycosides while retaining the anomeric stereochemistry. Notably, the key features of this protocol involve unprecedented long-range acyl transfer (from S/Se to O), thus affording acylation of the final product which is not yet reported by classical methods. This straightforward protocol offers a mild, short reaction time, synthetically simple approach, and compatibility with 8 types of sugar along with phenylthio/benzylseleno esters.

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A Facile Method for β‐Selenoglycoside Synthesis Using β‐p‐Methylbenzoyl Selenoglycoside as the Selenating Unit.

Cited by 2 publications

References 1 publication

Hepatoprotective effect of bis(4‐methylbenzoyl) diselenide against CCl₄‐induced oxidative damage in mice

Hepatoprotective effect of bis(4‐methylbenzoyl) diselenide against CCl₄‐induced oxidative damage in mice

Atom-Economic Synthesis of Unsymmetrical gem-Diarylmethylthio/Seleno Glycosides via Base Mediated C(O)–S/Se Bond Cleavage and Acyl Transfer Approach of Glycosylthio/Selenoacetates

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A Facile Method for β‐Selenoglycoside Synthesis Using β‐p‐Methylbenzoyl Selenoglycoside as the Selenating Unit.

Cited by 2 publications

References 1 publication

Hepatoprotective effect of bis(4‐methylbenzoyl) diselenide against CCl4‐induced oxidative damage in mice

Hepatoprotective effect of bis(4‐methylbenzoyl) diselenide against CCl4‐induced oxidative damage in mice

Atom-Economic Synthesis of Unsymmetrical gem-Diarylmethylthio/Seleno Glycosides via Base Mediated C(O)–S/Se Bond Cleavage and Acyl Transfer Approach of Glycosylthio/Selenoacetates

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Hepatoprotective effect of bis(4‐methylbenzoyl) diselenide against CCl₄‐induced oxidative damage in mice

Hepatoprotective effect of bis(4‐methylbenzoyl) diselenide against CCl₄‐induced oxidative damage in mice