Materials and biological applications of 1,2,3-selenadiazoles: a review

Joshi, Prasad G.; More, M.S.; Jadhav, Aditi A.; Khanna, Pawan K.

doi:10.1016/j.mtchem.2020.100255

Cited by 14 publications

(25 citation statements)

References 148 publications

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“…Organic compounds containing nitrogen–chalcogen (X–N, X = S, Se, Te) bonds are important structural units and are extensively noticed in inorganic and organic materials, catalysts, protein mimics, and potential drugs. 1–4 The popular methods for generation of compounds containing X–N bonds are ortho lithiation, chalcogen insertion, and oxidative cyclization of benzanilides, 5–8 or intramolecular cyclization of chalcogen acids. 9–11 As an alternative, transition metal-catalyzed direct cross-coupling of thiols and N–H compounds is rather beneficial due to the avoidance of using halogenated substrates during their synthesis.…”

Section: Introductionmentioning

confidence: 99%

Ligand-free access to benzisothiazolones and benzisoselenazolones through NiFe₂O₄ catalyzed concomitant annulation of 2-halobenzanilides with chalcogens and their late-stage transformations

2022

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Section: Introductionmentioning

confidence: 99%

Ligand-free access to benzisothiazolones and benzisoselenazolones through NiFe₂O₄ catalyzed concomitant annulation of 2-halobenzanilides with chalcogens and their late-stage transformations

2022

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“…The chalcogen-nitrogen bond (X-N, X = S, Se, Te) is an important motif in chemistry and is present in many different structures, ranging from inorganic and organic materials, catalysts, protein mimics, and drugs [1][2][3][4]. In the lab, the formation of a X-N bond is typically obtained from benzanilide, using ortholithiation, chalcogen insertion, and oxidative cyclization [5][6][7][8], and by intramolecular cyclocondensation of chalcogenic acids [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

“…In biochemistry and medicinal chemistry, besides ebselen and other GPx mimics, compounds based on heterocyclic scaffolds containing one or multiple Se-N bonds are being studied as antibiotic, antifungal, antiproliferative, anti-inflammatory, analgesic, and antimicrobial agents [1,3,17]. Particularly, selenazolinium salts appear as promising candidates in light of their good reactivity and selectivity toward thiol groups in peptides, proteins, and enzymes [35].…”

Section: Introductionmentioning

confidence: 99%

Chalcogen-Nitrogen Bond: Insights into a Key Chemical Motif

et al. 2021

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Chalcogen-nitrogen chemistry deals with systems in which sulfur, selenium, or tellurium is linked to a nitrogen nucleus. This chemical motif is a key component of different functional structures, ranging from inorganic materials and polymers, to rationally designed catalysts, to bioinspired molecules and enzymes. The formation of a selenium–nitrogen bond, typically occurring upon condensation of an amine and the unstable selenenic acid, often leading to intramolecular cyclizations, and its disruption, mainly promoted by thiols, are rather common events in organic Se-catalyzed processes. In this work, focusing on examples taken from selenium organic chemistry and biochemistry, the selenium–nitrogen bond is described, and its strength and reactivity are quantified using accurate computational methods applied to model molecular systems. The intermediate strength of the Se–N bond, which can be tuned to necessity, gives rise to significant trends when comparing it to the stronger S– and weaker Te–N bonds, reaffirming also in this context the peculiar and valuable role of selenium in chemistry and life.

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“…The chalcogen-nitrogen bond (X-N, X=S, Se, Te) is an important motif in chemistry present in many different structures, ranging from inorganic and organic materials, catalysts, protein mimics, and potential drugs [1][2][3][4]. In the lab, the formation of a X-N bond is typically obtained from benzanilide, using ortholithiation, chalcogen insertion, and oxidative cyclization [5][6][7][8], and by intramolecular cyclocondensation of chalcogenic acids [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

“…In biochemistry and medicinal chemistry, besides ebselen and other GPx mimics, compounds based on heterocyclic scaffolds containing one or multiple Se-N bonds are being studied as antibiotic, antifungal, anticancer, anti-inflammatory, analgesic, and antimicrobial agents [1,3,14]. Particularly, selenazolinium salts appear as promising candidates in light of their good reactivity and selectivity towards thiol groups in peptides, proteins and enzymes [23].…”

Section: Introductionmentioning

confidence: 99%

Chalcogen–Nitrogen Bond: Insights into a Key Chemical Motif

Rocha

Orian

Bortoli

et al. 2020

The 1st International Electronic Conference on Catalysis Sciences

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Chalcogen-nitrogen chemistry deals with systems in which sulfur, selenium or tellurium is linked to a nitrogen nucleus. This chemical motif is a key component of different functional structures, ranging from inorganic materials and polymers to rationally designed catalysts, to bioinspired molecules and enzymes. The formation of a selenium-nitrogen bond, and its disruption, are rather common events in organic Se-catalyzed processes. In nature, along the mechanistic path of glutathione peroxidase, evidence of the formation of a Se-N bond in highly oxidizing conditions has been reported and interpreted as a strategy to protect the selenoenzyme from overoxidation. Selenium is bonded to nitrogen also in the well-known ebselen, a selenenylamide with antioxidant, antimicrobic and cytoprotective activity and its formation/disruption has a crucial role for its pharmacological action. Focusing on examples taken from selenium organic chemistry and biochemistry, the selenium-nitrogen bond is described, and its strength and reactivity are quantified using accurate computational methods applied to model molecular systems. Significant trends show up when comparing to sulfur/tellurium-nitrogen bonds, reaffirming also in this context the peculiar and valuable role of selenium in chemistry and life

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Materials and biological applications of 1,2,3-selenadiazoles: a review

Cited by 14 publications

References 148 publications

Ligand-free access to benzisothiazolones and benzisoselenazolones through NiFe₂O₄ catalyzed concomitant annulation of 2-halobenzanilides with chalcogens and their late-stage transformations

Ligand-free access to benzisothiazolones and benzisoselenazolones through NiFe₂O₄ catalyzed concomitant annulation of 2-halobenzanilides with chalcogens and their late-stage transformations

Chalcogen-Nitrogen Bond: Insights into a Key Chemical Motif

Chalcogen–Nitrogen Bond: Insights into a Key Chemical Motif

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Materials and biological applications of 1,2,3-selenadiazoles: a review

Cited by 14 publications

References 148 publications

Ligand-free access to benzisothiazolones and benzisoselenazolones through NiFe2O4 catalyzed concomitant annulation of 2-halobenzanilides with chalcogens and their late-stage transformations

Ligand-free access to benzisothiazolones and benzisoselenazolones through NiFe2O4 catalyzed concomitant annulation of 2-halobenzanilides with chalcogens and their late-stage transformations

Chalcogen-Nitrogen Bond: Insights into a Key Chemical Motif

Chalcogen–Nitrogen Bond: Insights into a Key Chemical Motif

Contact Info

Product

Resources

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Ligand-free access to benzisothiazolones and benzisoselenazolones through NiFe₂O₄ catalyzed concomitant annulation of 2-halobenzanilides with chalcogens and their late-stage transformations

Ligand-free access to benzisothiazolones and benzisoselenazolones through NiFe₂O₄ catalyzed concomitant annulation of 2-halobenzanilides with chalcogens and their late-stage transformations