Synthesis and antimicrobial activity of selenazolidinone-4 derivatives

Levshin, I. B.; Tsurkan, A. A.; Rudzit, É. A.; Neshchadim, G. N.

doi:10.1007/bf00762895

Cited by 3 publications

(1 citation statement)

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“…Organoselenium chemistry has attracted increasing attention since selenium-containing compounds exhibit great diversity and wide applications in drug candidates, bioactive materials, and functional organic materials. − Furthermore, organoselenium compounds containing an isoselenourea skeleton have shown antitumor and antibacterium activities (Scheme ). However, the reported approaches to the synthesis of isoselenourea derivatives from easily handled materials under mild conditions are still rare. Therefore, development of an efficient approach for the synthesis of organic useful organoselenium compounds bearing an isoselenourea skeleton is of great significance.…”

Section: Introductionmentioning

confidence: 99%

Copper(I)-Catalyzed Ligand-Promoted Multicomponent Reactions of Isocyanides, Selenium, Amines, and Iodoarenes: Access to Highly Functionalized Carbamimidoselenoates

et al. 2017

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A new and facile approach toward highly functionalized carbamimidoseleknoates was developed through the copper(I)-catalyzed ligand-promoted four-component reaction of isocyanides, selenium, amines, and aryl iodides. The reaction constructed a range of organoselenium compounds containing an isoselenourea skeleton with potential bioactivity directly from selenium powder. The simplicity of method and broad diversity of substrates also highlight this work.

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Section: Introductionmentioning

confidence: 99%

Copper(I)-Catalyzed Ligand-Promoted Multicomponent Reactions of Isocyanides, Selenium, Amines, and Iodoarenes: Access to Highly Functionalized Carbamimidoselenoates

et al. 2017

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BF₃ ⋅ OEt₂ Catalyzed Synthesis of 1,3‐Thiazines/‐Selenazines

2020

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An efficient strategy for the synthesis of 3,4dihydro-2H-1,3-thiazines / 3,4-dihydro-2H-1,3-selenazines from propargylic alcohols and thioamides/thiosemicarbazones/selenamides is described. The reaction is accomplished in moderate to excellent yield under mild conditions that did not require the exclusion of air or moisture and offers an operationally simplistic and convenient route to the synthetically useful six-membered N,S/Se-heterocycles. 1,3-Thiazines are attractive six-membered N,S-heterocyclic scaffolds for medicinal chemistry. [1] Compounds bearing this subunit often exhibit antiarrhythmic, antispasmodic, angiogenic, and antibiotic activities [2] and are also used as precursors for the preparation of other heterocyclic biomolecules, such as cephalosporins (Figure 1) or 1,4-thiazepines. [3] For example, some derivatives of thiazine are cannabinoid receptor agonists, [4] antihypotensive, [5] antitubercular, [6] and antibacterial [7] agents. Further, thiazine derivatives can be used for gastrointestinal disorders [8] or diabetes [9] prevention. Fused heterocyclic systems possessing thiazine ring have been reported as antioxidants, [10] analgesic, anti-inflammatory agents, [11] or calcium channel modulators. [12] Additionally, organoselenium compounds are full of diversity and specialized wide applications such as selenium-based safety-catch linkers [13a] for the solid-phase semisynthesis of vancomycin, asymmetric carboselenylation, [13b] selenocyclizations, [13c] selenium promoted carbocyclization [13d] and acts as catalysts in organic synthesis. [13e,f] Isoselenourea derivatives also show encouraging effects on the antitumor activity (Figure 1). [14] Selenazines have attracted much attention in dyes [15,16] and medicinal fields (antibacterial effects against Escherichia coli and Staphylococcus aureus, [17] inhibitory effects on the proliferation of human HT-1080 fibrosarcoma cells, [18] protein kinase inhibition, [19] and as antitumor agents [20]). Although syntheses of oxazines [21,22] are well known, but the corresponding thiazines and selenazines have been limited, [23] owing to difficulties in the preparation of sulphur and selenium-containing starting materials. Nevertheless, only a few [a]

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Base-promoted cascade reaction of isocyanides, selenium and amines: a practical approach to 2-aminobenzo[d][1,3]selenazines under metal-free conditions

et al. 2015

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Synthesis and antimicrobial activity of selenazolidinone-4 derivatives

Cited by 3 publications

References 2 publications

Copper(I)-Catalyzed Ligand-Promoted Multicomponent Reactions of Isocyanides, Selenium, Amines, and Iodoarenes: Access to Highly Functionalized Carbamimidoselenoates

Copper(I)-Catalyzed Ligand-Promoted Multicomponent Reactions of Isocyanides, Selenium, Amines, and Iodoarenes: Access to Highly Functionalized Carbamimidoselenoates

BF₃ ⋅ OEt₂ Catalyzed Synthesis of 1,3‐Thiazines/‐Selenazines

Base-promoted cascade reaction of isocyanides, selenium and amines: a practical approach to 2-aminobenzo[d][1,3]selenazines under metal-free conditions

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Synthesis and antimicrobial activity of selenazolidinone-4 derivatives

Cited by 3 publications

References 2 publications

Copper(I)-Catalyzed Ligand-Promoted Multicomponent Reactions of Isocyanides, Selenium, Amines, and Iodoarenes: Access to Highly Functionalized Carbamimidoselenoates

Copper(I)-Catalyzed Ligand-Promoted Multicomponent Reactions of Isocyanides, Selenium, Amines, and Iodoarenes: Access to Highly Functionalized Carbamimidoselenoates

BF3 ⋅ OEt2 Catalyzed Synthesis of 1,3‐Thiazines/‐Selenazines

Base-promoted cascade reaction of isocyanides, selenium and amines: a practical approach to 2-aminobenzo[d][1,3]selenazines under metal-free conditions

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BF₃ ⋅ OEt₂ Catalyzed Synthesis of 1,3‐Thiazines/‐Selenazines