Discovery of SY-5609: A Selective, Noncovalent Inhibitor of CDK7

Journal of Medicinal Chemistry, Journal Year: 2021, Volume and Issue: 65(2), P. 1458 - 1480

Published: Nov. 2, 2021

CDK7 has emerged as an exciting target in oncology due to its roles two important processes that are misregulated cancer cells: cell cycle and transcription. This report describes the discovery of

Language: Английский

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Ruthenium‐Catalyzed Enantioselective Propargylic Phosphinylation of Propargylic Alcohols with Phosphine Oxides

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(20), P. 11231 - 11236

Published: April 7, 2021

Abstract The development of transition metal‐catalyzed enantioselective propargylic substitution reactions has gained much progress in recent years, however, no successful example with phosphorus‐centered nucleophiles yet been reported until now. Herein, we report the first ruthenium‐catalyzed alcohols diarylphosphine oxides as nucleophiles. This synthetic approach provides a new method to prepare chiral phosphorus‐containing organic compounds.

Language: Английский

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From rocks to bioactive compounds: a journey through the global P(v) organophosphorus industry and its sustainability

RSC Sustainability, Journal Year: 2022, Volume and Issue: 1(1), P. 11 - 37

Published: Nov. 4, 2022

This tutorial review showcases the diversity & utility of organophosphorus molecules, focusing on P( v ) structures. Their rich nomenclature, application industrial synthesis will be highlighted within context sustainable chemistry.

Language: Английский

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Access to Phosphine-Containing Quinazolinones Enabled by Photo-Induced Radical Phosphorylation/Cyclization of Unactivated Alkenes

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(15), P. 10146 - 10157

Published: July 13, 2022

A mild and facile photo-induced cascade radical addition/cyclization of unactivated alkenes has been reported, through which a variety biologically valuable phosphine-containing quinazolinones could be obtained in moderate to good yields. The protocol was characterized by conditions, broad substrate scope, high atomic economy.

Language: Английский

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Harvesting phosphorus-containing moieties for their antibacterial effects

Bioorganic & Medicinal Chemistry, Journal Year: 2023, Volume and Issue: 96, P. 117512 - 117512

Published: Nov. 2, 2023

Clinically manifested resistance of bacteria to antibiotics has emerged as a global threat society and there is an urgent need for the development novel classes antibacterial agents. Recently, use phosphorus in agents been explored quite unprecedent manner. In this comprehensive review, we summarize phosphorus-containing moieties (phosphonates, phosphonamidates, phosphonopeptides, phosphates, phosphoramidates, phosphinates, phosphine oxides, phosphoniums) compounds with effect, including their β-lactamase inhibitors disinfectants. We show that can serve pharmacophores, bioisosteres, prodrugs modify pharmacodynamic pharmacokinetic properties. further discuss mechanisms action, biological activities, clinical highlight possible future prospects.

Language: Английский

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Expedient radical phosphonylations via ligand to metal charge transfer on bismuth

Chemical Science, Journal Year: 2024, Volume and Issue: 15(19), P. 7136 - 7143

Published: Jan. 1, 2024

Herein, we have developed efficient radical phosphonylations tailored upon visible-light mediated LMCT on bismuth. Phosphonylation of a broad range substrate classes was carried out under mild energy conditions using BiCl 3 as the catalyst.

Language: Английский

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Shining Light on the Light-Bearing Element: A Brief Review of Photomediated C–H Phosphorylation Reactions

Synthesis, Journal Year: 2020, Volume and Issue: 53(06), P. 1003 - 1022

Published: Nov. 23, 2020

Abstract Organophosphorus compounds have numerous useful applications, from versatile ligands and nucleophiles in the case of trivalent organophosphorus species to therapeutics, agrochemicals material additives for pentavalent species. Although phosphorus chemistry is a fairly mature field, construction C–P(V) bonds relies heavily on either prefunctionalized substrates such as alkyl or aryl halides, requires previously oxidized C=N C=O, leading potential sustainability issues when looking at overall synthetic route. In light recent advances photochemistry, using photons reagent can provide better alternatives phosphorylations by unlocking radical mechanisms providing interesting redox pathways. This review will showcase different photomediated phosphorylation procedures available converting C–H into bonds. 1 Introduction 1.1 Compounds 1.2 Phosphorylation: Construction Bonds 1.3 Photochemistry an Alternative Classical Phosphorylations 2 Ionic Mechanisms Involving Nucleophilic Additions 3 Radical Intermediates 3.1 Reactive Carbon Radicals 3.2 Phosphorus 3.2.1 Photoredox: Direct Creation 3.2.2 Indirect 3.2.3 Dual Catalysis 3.3 Photolytic Cleavage 4 Conclusion Outlook

Language: Английский

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Easily Available, Amphiphilic Diiron Cyclopentadienyl Complexes Exhibit in Vitro Anticancer Activity in 2D and 3D Human Cancer Cells through Redox Modulation Triggered by CO Release

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(39), P. 10169 - 10185

Published: June 9, 2021

A straightforward two-step procedure via single CO removal allows the conversion of commercial [Fe2 Cp2 (CO)4 ] into a range amphiphilic and robust ionic complexes based on hybrid aminocarbyne/iminium ligand, (CO)3 {CN(R)(R')}]X (R, R'=alkyl or aryl; X=CF3 SO3 BF4 ), up to multigram scales. Their physicochemical properties can be modulated by an appropriate choice N-substituents counteranion. Tested against panel human cancer cell lines, were shown possess promising antiproliferative activity circumvent multidrug resistance. Interestingly, most derivatives also retained significant cytotoxic 3D cultures. Among them, complex with R=4-C6 H4 OMe R'=Me emerged as best performer series, being average about six times more active cells than noncancerous line, displayed IC50 values comparable those cisplatin in Mechanistic studies revealed ability release carbon monoxide act oxidative stress inducers cells.

Language: Английский

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Electron Donor‐Acceptor Complex Initiated Photochemical Phosphorus Arylation with Diaryliodonium Salts toward the Synthesis of Phosphine Oxides

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(11), P. 1893 - 1900

Published: May 20, 2023

Abstract Arylation of amino‐, diamino‐ and triaminophosphines with aryl(mesityl)iodonium triflates under blue light irradiation followed by oxidative P−N bond cleavage in the situ generated amino phosphonium salts hydrolytic conditions represent a method for synthesis substituted arylphosphine oxides, arylphosphinic arylphosphonic amides respectively. The proposed approach is based on using visible as only promoter C−P formation, accommodates variety functional groups, can be applied to late‐stage C−H functionalization drug molecules.

Language: Английский

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Borrowing Hydrogen β-Phosphinomethylation of Alcohols Using Methanol as C1 Source by Pincer Manganese Complex

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(47), P. 25545 - 25552

Published: Nov. 14, 2023

Herein, we report a manganese-catalyzed three-component coupling of β-H containing alcohols, methanol, and phosphines for the synthesis γ-hydroxy via borrowing hydrogen strategy. In this development, methanol serves as sustainable C1 source. A variety aromatic aliphatic substituted alcohols could undergo dehydrogenative cross-coupling process efficiently deliver corresponding β-phosphinomethylated alcohol products in moderate to good yields. Mechanistic studies suggest that transformation proceeds sequential manner including catalytic dehydrogenation, aldol condensation, Michael addition, hydrogenation.

Language: Английский

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