Selenization of Small Molecule Drugs: A New Player on the Board

Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 67(10), P. 7759 - 7787

Published: May 8, 2024

There is an urgent need to develop safer and more effective modalities for the treatment of a wide range pathologies due increasing rates drug resistance, undesired side effects, poor clinical outcomes, etc. Throughout years, selenium (Se) has attracted great deal attention its important role in human health. Besides, growing body work unveiled that inclusion Se motifs into number molecules promising strategy obtaining novel therapeutic agents. In current Perspective, we have gathered most recent literature related incorporation different moieties scaffolds known drugs their feasible pharmaceutical applications. addition, highlight representative examples as well provide our perspective on possible future directions, promises, opportunities, challenges this ground-breaking area research.

Language: Английский

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Direct Functionalization of para‐Quinones: A Historical Review and New Perspectives

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(27)

Published: May 21, 2024

Abstract The direct functionalization of quinones has always fascinated research communities due to their biological and redox activities subsequent application. Quinone motifs play a vital role as precursors for many bioactive compounds materials; hence, ingenious methodologies have been elaborated exploring these units. A significant part the synthetic strategies towards functionalized achieved by installing substituents on hydroquinones, phenols, or quinone itself different oxidative coupling reactions via radical pathways with without utilization metal catalysts. simple C−H bond remains challenging inherited electronic nature high dissociation energy. This review article summarizes recent advancement made through quinones. Our primary focus will be approaches mechanistic that appeared in last two decades, along short historical importance family.

Language: Английский

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CuBr₂-Catalyzed Annulation of 2-Bromo-N-Arylbenzimidamide with Se/S₈ Powder for the Synthesis of Benzo[d]isoselenazole and Benzo[d]isothiazole

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(4), P. 1963 - 1976

Published: Jan. 31, 2023

A CuBr2-catalyzed annulation of 2-bromo-N-arylbenzimidamide with selenium/sulfur powder for the synthesis benzo[d]isoselenazole and benzo[d]isothiazole in generally good yields was investigated. This synthetic strategy features substrate scope functional group tolerance. Furthermore, corresponding products could be converted into N-aryl indoles via rhodiumIII-catalyzed ortho C-H activation N-phenyl ring, providing an efficient approach axial aromatic molecules.

Language: Английский

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Directing Group Strategy for the Isolation of Organoselenium(VI) Benzoselenonates: Metal-Free Catalysts for Hydrogen Evolution Reaction

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 146(1), P. 57 - 61

Published: Dec. 18, 2023

The exploration of fourth-period organoelements, particularly organoseleniums in their highest VI oxidation state, is limited owing to stability and synthesis. Herein, the isolation a new class quinolinyl-embedded, hexavalent selenium(VI) benzoselenonates has been discussed further evaluated for metal-free electrocatalytic hydrogen evolution reaction (HER). Se(VI) exhibited high Faradaic efficiency (F.E.) H2 gas production up 86% with very good turnover number (TON) 43 moderate overpotential (η) 500 mV; presence mild acetic acid source less deprotonating DMF solvent. Taken together various (NMR, UV–vis, EPR) spectroscopic DFT computation studies, plausible HER pathway proposed, which suggests that electrochemical reduction quinolinyl ring initiation step acts as site by involving hydridic type intermediate generation.

Language: Английский

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Introduction of Methyl Group in Substituted Isoselenazolones: Catalytic and Mechanistic Study

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4273 - 4285

Published: March 17, 2023

Copper-catalyzed direct selenation of substituted 2-bromo-N-phenylbenzamide substrates with elemental selenium powder provided a series methoxy-substituted isoselenazolones via the C-Se and Se-N bond formations. Phenolic have been obtained by O-demethylation corresponding analogues using boron tribromide. Some structurally characterized X-ray single-crystal analysis. The glutathione peroxidase (GPx)-like antioxidant activity has evaluated both in thiophenol coupled-reductase assays. All showed good GPx-like activities assay. ferric-reducing power phenolic antioxidants also evaluated. best were found to be agents. single electron transfer, hydrogen atom proton-coupled transfer mechanisms for properties all catalysts supported density functional theory calculations. catalytic cycle was proposed one involving diselenide, selenenyl sulfide, selenol, selenenic acid as intermediates 77Se{1H} NMR spectroscopy.

Language: Английский

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2‐Benzamide Tellurenyl Iodides: Synthesis and Their Catalytic Role in CO₂ Mitigation

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(49)

Published: June 20, 2023

Benzamide-derived organochalcogens (chalcogen=S, Se, and Te) have shown promising interest in biological synthetic chemistry. Ebselen molecule derived from benzamide moiety is the most studied organoselenium. However, its heavier congener organotellurium under-explored. Here, an efficient copper-catalyzed atom economical method has been developed to synthesize 2-phenyl-benzamide tellurenyl iodides by inserting a tellurium into carbon-iodine bond of 2-iodobenzamides one pot with 78-95 % yields. Further, Lewis acidic nature Te center basic nitrogen synthesized 2-Iodo-N-(quinolin-8-yl)benzamide enabled them as pre-catalyst for activation epoxide CO2 at 1 atm preparation cyclic carbonates TOF TON values 1447 h-1 4343, respectively, under solvent-free conditions. In addition, 2-iodo-N-(quinolin-8-yl)benzamide also used activating anilines form variety 1,3-diaryl ureas up 95 yield. The mechanistic investigation mitigation done 125 NMR HRMS studies. It seems that reaction proceeds via formation catalytically active Te-N heterocycle, ebtellur intermediate which isolated structurally characterized.

Language: Английский

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Urea Hydrogen Peroxide and Ethyl Lactate, an Eco-Friendly Combo System in the Direct C(sp²)–H Bond Selenylation of Imidazo[2,1-b]thiazole and Related Structures

ACS Omega, Journal Year: 2023, Volume and Issue: 8(42), P. 39535 - 39545

Published: Oct. 12, 2023

Herein, we describe a urea hydrogen peroxide-mediated sustainable protocol for the synthesis of selenylated imidazo[2,1-b]thiazole by using half molar equivalent diorganyl diselenides in ethyl lactate as greener solvent. The reaction features high yields, easy performance on gram scale, metal-free conditions, well applicability to imidazopyridine and imidazopyrimidine.

Language: Английский

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Recent progress in the organoselenium-catalyzed difunctionalization of alkenes

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Selenium-based catalysts have recently been utilized to facilitate a variety of new organic transformations, owing their intrinsic advantages, including low cost, toxicity, stability in both air and water, strong compatibility with diverse functional groups. The difunctionalization alkenes-the process incorporating two groups onto carbon-carbon double bond-has garnered particular interest within the chemical community its significant applications synthesis. Recently, organoselenium-catalyzed alkenes has emerged as an ideal powerful route obtain high-value vicinal difunctionalized molecules. This review emphasizes recent advancements this rapidly evolving field, focusing on scope, limitations, mechanisms various reactions.

Language: Английский

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Glutathione Peroxidase-like Antioxidant Activity of 1,3-Benzoselenazoles: Synthesis and In Silico Molecular Docking Studies as Pancreatic Lipase Inhibitors

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 16934 - 16948

Published: Nov. 27, 2023

The synthesis of 1,3-benzoselenazoles was achieved by the reaction corresponding bis[3-amino-N-(p-tolyl)benzamide-2-yl] diselenide, bis[3-amino-N-(4-methoxyphenyl)benzamide-2-yl] and bis[3-amino-N-(4-(dimethylamino)phenyl) benzamide-2-yl] diselenide with aryl aldehydes. continued to exist as planar molecules due presence secondary Se···O interactions revealed single-crystal X-ray analysis. in confirmed using natural bond orbital (NBO) atoms (AIM) calculations. Nucleus-independent chemical shift (NICS) values suggested aromatic character a five-membered benzoselenazole heterocyclic ring. glutathione peroxidase (GPx)-like antioxidant activity all assessed thiophenol assay, exhibiting greater than Ph2Se2 used reference. most active catalyst carrying strong electron-donating group (–NMe2) at ortho-position ring further investigated different concentrations thiophenol, H2O2, for determining their catalytic parameters. Moreover, potential applications against pancreatic lipase (PL) have been identified silico between sites 1LPB protein evaluated molecular docking study.

Language: Английский

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Asymmetric Carbene Insertion into Se‐S Bonds by Synergistic Rh(II)/Guanidine Catalysis Involving Chalcogen‐Bond Assistance

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 2, 2024

The efficient construction of chalcogen-atom-based chiral compounds remains a challenge, despite the importance organoselenium and organosulfur in life materials science. Chalcogen atoms can form net attractive interactions called chalcogen bonds, but it is an undeveloped tool to assist asymmetric catalysis. Herein, we report enantioselective insertion platform install stereogenic center bearing selenyl thiocyano functional groups. Our method operates by synergistic catalysis guanidine achiral dirhodium complex three-component or four-component reaction, through Se-S bond into carbene species, competing successfully with spontaneous racemic process showing high regioselectivity. As elucidated spectroscopic experiments computational studies, unique mechanism involving as well hydrogen bonding was established account for enantiocontrol. stereoselectivity holds broad array selenylthiocyanatopropanoates, which showed excellent anti-inflammatory toward IL-1β low cytotoxicity.

Language: Английский

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