Journal of Organometallic Chemistry, Год журнала: 2022, Номер 979, С. 122510 - 122510
Опубликована: Сен. 5, 2022
Язык: Английский
Chemistry - A European Journal, Год журнала: 2024, Номер 30(23)
Опубликована: Фев. 22, 2024
A safe and efficient method for the in-situ preparation of (diazomethyl)dimethylphosphine oxide - a hereto unexplored diazoalkane reagent is developed. The based on diazotization corresponding P(O)Me
Язык: Английский
Процитировано
2
Journal of Medicinal Chemistry, Год журнала: 2024, Номер 67(17), С. 15131 - 15147
Опубликована: Сен. 2, 2024
A series of arylsulfones and heteroarylsulfones have previously been demonstrated to dysregulate the conserved bacterial ClpP protease, causing unspecific degradation essential cellular housekeeping proteins ultimately resulting in cell death. cocrystal structure a 2-β-sulfonylamide analog, ACP1-06, with Escherichia coli showed that its 2-pyridyl sulfonyl substituent adopts two orientations binding site related through sulfone bond rotation. From this, new bis-aryl phosphine oxide scaffold, designated as ACP6, was designed based on "conformation merging" approach dual orientation ACP1-06 sulfone. One ACP6-12, exhibited over 10-fold increase activity parent compound, X-ray confirmed predicted conformation. This allowed for comparative analysis how different ligand classes bind hydrophobic site. The study highlights successful application structure-based rational design novel oxide-based antibiotics.
Язык: Английский
Процитировано
2
The Journal of Organic Chemistry, Год журнала: 2022, Номер 88(1), С. 1 - 17
Опубликована: Ноя. 18, 2022
The previously unknown difluoromethyl diazirines and the neglected trifluoromethyl-aliphatic were synthesized characterized. Model photolabeling experiments biological studies showed that these compounds could indeed be used as photoaffinity labels.
Язык: Английский
Процитировано
8
Angewandte Chemie, Год журнала: 2022, Номер 135(3)
Опубликована: Окт. 13, 2022
Abstract Sulfonylated aromatics are commonplace motifs in drugs and agrochemicals. However, methods for the direct synthesis of sulfonylated non‐classical arene bioisosteres, which could improve physicochemical properties drug agrochemical candidates, limited. Here we report a solution to this challenge: one‐pot halosulfonylation [1.1.1]propellane, [3.1.1]propellane bicyclo[1.1.0]butanes that proceeds under practical, scalable mild conditions. The sulfonyl halides used chemistry feature aryl, heteroaryl alkyl substituents, conveniently generated situ from readily available sulfinate salts halogen atom sources. This methodology enables an array pharmaceutically agrochemically relevant halogen/sulfonyl‐substituted bioisosteres cyclobutanes, on up multidecagram scale.
Язык: Английский
Процитировано
6
Journal of organic and pharmaceutical chemistry, Год журнала: 2023, Номер 21(2), С. 41 - 52
Опубликована: Авг. 21, 2023
Aim. To synthesize a hybrid molecular platform incorporating dimethylphosphinoyl and 4,5-dihydroisoxazole moieties suitable for the creation of focused combinatorial libraries compounds.Results discussion. The base-promoted interaction halogenoxides with dimethyl(vinyl)phosphine oxide under mild conditions allowed us to obtain 11 isoxazoline–dimethylphosphine hybrids in moderate yields. reaction was found be regio- though non-stereoselective. Furoxans were identified as possible side products reaction.Experimental part. one-pot used synthesis target compounds. Nitrile oxides obtained situ from corresponding halogenoximes by generation. ADME parameters synthesized 5-P(O)Me2-isoxazoline compared its isosters same core structure predicted using SwissADME Web Tool. compounds characterized 1H, 13C, 19F, 31P NMR spectroscopy HPLC-MS spectrometry methods, well elemental analysis.Conclusions. A practical approach isoxazoline decorated 5-P(O)Me2 “magic” group containing 3-substituent an easy-to-modify functionality has been developed. On example piperidine derivative, effect on physicochemical properties determined.
Язык: Английский
Процитировано
2
Organic Letters, Год журнала: 2024, Номер unknown
Опубликована: Дек. 6, 2024
A series of 3-phosphonyl polysubstituted pyridine were first synthesized by photocatalysis, combining a phosphonyl radical cascade reaction, Boc deprotection, and aromatization. This strategy can avoid the difficulties activating C3-H bond on to synthesize 3-phosphonylpyridine under mild conditions. Furthermore, constructing different enynes, we achieve metal-free modular synthesis pyridine, which will be transferred into new type phosphine ligand. is significance for organometallic catalysis. The regioselective control detailed reaction mechanism are explained DFT calculations.
Язык: Английский
Процитировано
0
Royal Society of Chemistry eBooks, Год журнала: 2024, Номер unknown, С. 26 - 57
Опубликована: Фев. 21, 2024
This chapter gives an account of newer developments in the synthesis and reactivity phosphine chalcogenides, mainly oxides sulfides, during 2020. A series new synthetic methods for is discussed, followed by preparations utilizing simple P-reagents such as P(iii)- P(v)-chlorides, >P(O)H species. Their additions to unsaturated substrates P–C coupling reactions, involving interesting variations, represent a hot topic. The modification P-chalcogenides including deoxygenations are also shown. Optically active their complexes form usual part this chapter.
Язык: Английский
Процитировано
0
Journal of Organometallic Chemistry, Год журнала: 2022, Номер 979, С. 122510 - 122510
Опубликована: Сен. 5, 2022
Язык: Английский
Процитировано
2