683-08-9Relevant articles and documents
Synthesis of 2-(Thiophen-3-yl)vinylphosphonic acid
Linzaga-Elizalde, Irma,Escalante, Jaime,Nicho, Maria E.,Gueizado-Rodriguez, Marisol
, p. 1511 - 1515 (2009)
A simple and efficient synthesis of 2-(thiophen-3-yl)vinylphosphonic acid has been developed. The title compound is obtained in 70% yield by addition of thiophene-3-carbaldehyde to lithium diethyl methylenephosphonate, followed by dehydration and hydrolysis. 1H, 13C, and 31P NMR spectra are presented for each of the intermediates. Copyright Taylor & Francis Group, LLC.
Intramolecular O → Si donor-acceptor interaction in R 2P(=O)CH2CH2SiF3 molecules: Synthesis of dialkyl [2-(trifluorosilyl)ethyl]phosphonate and bis[(chloromethyl)dimethylsilyl] styrylphosphonate
Voronkov,Pestunovich,Chernov,Albanov,Belogolova,Klyba,Pestunovich
, p. 1554 - 1561 (2006)
The reaction of diethyl [2-(triethoxysilyl)ethyl]phosphonate with boron trifluoride etherate was used to synthesize diethyl [2-(trifluorosilyl)ethyl] phosphonate. The reaction of bis(trimethylsilyl) styrylphosphonate with chloro(chloromethyl)dimethylsilane gave bis[(chloromethyl)dimethylsilyl] styrylphosphonate. Multinuclear 1H, 13C, 19F, 29Si, and 31P NMR spectroscopy established the absence of a P=O → Si coordination bond in these compounds and the four-coordinate state of the silicon atom. Evidence for this finding was obtained by B3LYP/6-31G(d) quantum-chemical calculations. However, the same calculations for R2P(=O)? CH2CH2SiF3 (R = Me, Me2N) showed the presence in such molecules of an O → Si coordination bond both in the gas phase and in CHCl3 solution. The distance between the O and Si atoms in this series molecules decreases with R in the order: MeO > Me > Me2N. The axial Si-F bond length increases in the same order and parallels the order of the Hammet σ 0 m constants of these substituents, relating to their interaction with π-electron systems. Nauka/Interperiodica 2006.
Access to chiral α-substituted-β-hydroxy arylphosphonates enabled by biocatalytic dynamic reductive kinetic resolution
Chen, Fener,Huang, Zedu,Li, Zihan,Tao, Yuan,Wang, Zexu,Wu, Xiaofan,Yu, Xiaomin,Zeng, Yiping
supporting information, p. 2672 - 2677 (2020/04/17)
Ketoreductase (KRED)-catalyzed dynamic reductive kinetic resolution (DYRKR) of α-substituted-β-keto arylphosphonates was developed as a generic and stereoselective approach to synthesize chiral α-substituted-β-hydroxy arylphosphonates, with moderate-to-excellent isolated yield (up to 96%), good-to-excellent diastereoselectivity (up to >99 : 99% ee) being achieved.
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.
