5284-12-8Relevant academic research and scientific papers
Light-Enabled Radical 1,4-Aryl Migration Via a Phospho-Smiles Rearrangement
De Abreu, Maxime,Belmont, Philippe,Brachet, Etienne
, p. 3758 - 3767 (2021/02/01)
Rearrangement reactions in organic chemistry are attractive strategies to build efficiently complex scaffolds, in just one step, from simple starting materials. Among them, aryl migrations are certainly one of the most useful and straightforward rearrangement for building attractive carbon-carbon bonds. Of note, anionic aryl migration reactions have been largely described compared to their radical counterparts. Recently, visible-light catalysis has proven its efficiency to generate such radical rearrangements due to the concomitant loss of a particle (often CO2 or SO2), which is the driving-force of the reaction. Here, we disclose a Smiles-type rearrangement, triggered by a phosphorus-containing unit (arylphosphoramidate), therefore called "phospho-Smiles"rearrangement, allowing a Csp2-Csp2 bond formation thanks to a 1,4-aryl migration reaction. In addition, combining this approach with a radical hydroamination/amination reaction produces an amination/phospho-Smiles cascade particularly attractive, for instance, to investigate the synthesis of the phthalazine core, a scarcely described scaffold of interest for medicinal chemistry projects.
Transition Metal-Free Synthesis of α-Aminophosphine Oxides through C(sp3)?P Coupling of 2-Azaallyls
Wang, Jing,Deng, Guogang,Liu, Chunxiang,Chen, Zhuo,Yu, Kaili,Chen, Wen,Zhang, Hongbin,Yang, Xiaodong
supporting information, p. 2268 - 2273 (2020/03/04)
Radical reactions have been widely applied in C?P bond-forming strategies. Most of these strategies require initiators, transition metal catalysts, or organometallic reagents. Herein, a transition metal-free C(sp3)?P bond formation to prepare α
Enantiodivergent Synthesis of Both PAMPO Enantiomers Using l -Menthyl Chloroacetate and Stereomutation at P in Classical Quaternisation Reactions
Dziuba, Kamil,Lubańska, Ma?gorzata,Pietrusiewicz, K. Micha?
, p. 909 - 916 (2020/03/13)
A practical protocol for efficient synthesis of both PAMPO enantiomers as well as related functionalised P-stereogenic phosphine oxides in 1-3 steps from effectively resolved (S P)- l -menthyl o -anisyl-(phenyl)phosphinylacetate has been develo
Discovery of phosphonamidate IDO1 inhibitors for the treatment of non-small cell lung cancer
Du, Qianming,Feng, Xi,Wang, Yinuo,Xu, Xi,Zhang, Yan,Qu, Xinliang,Li, Zhiyu,Bian, Jinlei
, (2019/08/26)
Targeting indoleamine 2,3-dioxygenase 1 (IDO1) has been identified as an attractive approach for the development of cancer immunotherapy. In this study, a series of phosphonamidate ester containing compounds were designed, synthesized and evaluated for their inhibitory activities against IDO1. Among them, compounds 16, 17, and 26 with good IDO1 inhibitory (HeLa IDO1 IC50 = 10–21 nM, hIDO1 IC50 = 78–121 nM) activities were selected for further investigation and showed good physicochemical properties. Furthermore, based on comparable PK profile and excellent IDO2/TDO inhibitory potency, representative compound 16 was selected for further bio-evaluation and characterized with good efficacy in suppressing lung metastasis (77% inhibition rate) of Lewis cells in vivo. Thus, compound 16 could be a potential and efficacious agent for further evaluation.
Synthesis and evaluation of phosphorus containing, specific CDK9/CycT1 inhibitors
Németh, Gábor,Greff, Zoltán,Sipos, Anna,Varga, Zoltán,Székely, Rita,Sebestyén, Mónika,Jászay, Zsuzsa,Béni, Szabolcs,Nemes, Zoltán,Pirat, Jean-Luc,Volle, Jean-No?l,Virieux, David,Gyuris, ágnes,Kelemenics, Katalin,áy, éva,Minarovits, Janos,Szathmary, Susan,Kéri, Gy?rgy,Orfi, László
, p. 3939 - 3965 (2014/06/09)
Although there is a significant effort in the design of a selective CDK9/CycT1 inhibitor, no compound has been proven to be a specific inhibitor of this kinase so far. The aim of this research was to develop novel and selective phosphorus containing CDK9/CycT1 inhibitors. Molecules bearing phosphonamidate, phosphonate, and phosphinate moieties were synthesized. Prepared compounds were evaluated in an enzymatic CDK9/CycT1 assay. The most potent molecules were tested in cell-based toxicity and HIV proliferation assays. Selectivity of shortlisted compounds against CDKs and other kinases was tested. The best compound was shown to be a highly specific, ATP-competitive inhibitor of CDK9/CycT1 with antiviral activity.
N-Alkyl-N'-[(alkyl/aryl)(alkoxy/aroxy)phosphoryl]ureas: Synthesis and extraction properties toward f-elements
Goryunov,Baulina,Goryunova,Matveeva,Safiulina,Nifant'ev
, p. 141 - 148 (2014/11/27)
A reaction of chlorophosphonates R1R2P(O)Cl with NaOCN and subsequent treatment with octylamine lead to phosphorylureas R 1R2P(O)NHC(O)NHC8H17-n (R 1 = EtO, PhO; R2 = Me, Ph). Their extraction capability toward UVI and a number of tervalent lanthanides (LaIII, NdIII, HoIII, YbIII) was studied. Efficiency and selectivity of these ligands in the extraction of f-elements from nitric acid solutions to chloroform were compared with extraction properties of a model phosphine oxide-type phosphorylurea MePhP(O)NHC(O)NHC8H 17-n and carbamoylphosphine oxide Ph2P(O)CH 2C(O)NBu2.
Surface-mediated synthesis of organophosphorus-based hydrazides using basic alumina
Kavita,Joshi,Sharma,Joshi
scheme or table, p. 1034 - 1039 (2011/02/16)
The surface-mediated synthesis of O-alkyl alkylphosphorohydrazides and N,N-dialkylamino alkylphosphorohy- drazides from phosphoryl chlorides is described. The effect of the presence of chromatographic-grade Al 2O3 (basic) on the hydr
Electroactive poly zinc, cadmium, manganese ferrocenylphenylphosphinates
Oms, Olivier,Bideau, Jean Le,Vioux, André,Leclercq, Dominique
, p. 363 - 370 (2007/10/03)
The synthesis of ferrocenylphenylphosphinic acid in high yield is reported. The electrochemical behaviour of ethyl ferrocenylphenylphosphinate, ferrocenylphenylphosphinic acid and its sodium salt are compared. The preparation and characterization of zinc,
Intramolecular Hydrogen-bond Participation in Phosphonylammonium Salt Formation
Smith III, Amos B.,Ducry, Laurent,Corbett, R. Michael,Hirschmann, Ralph
, p. 3887 - 3890 (2007/10/03)
equation presented A series of phosphonochloridates and phosphonyl dichlorides were prepared, and their reactivity with triethylamine has been investigated using 31P NMR spectroscopy. Taken together these studies provide evidence that an intram
