1363568-19-7Relevant academic research and scientific papers
New promising generation of phosphates α-aminophosphonates: Design, synthesis, in-vitro biological evaluation and computational study
Adamiak, Marta,Aissa, Rim,Aribi-Zouioueche, Louisa,Gali, Lynda,Guezane-Lakoud, Samia,Guillot, Regis,Ignaczak, Anna,Merabet-Khelassi, Mounia,Toffano, Martial
, (2021/09/20)
A novel category of phosphate-phosphonate compounds is synthesized by a sequence multicomponent reactions strategy of Kabachnik-Fields and Atherton-Todd reactions. All the designed products are obtained with good chemical yields in short reaction times, and confirmed by spectroscopy analyses. The diethyl [(4-diethylphosphate phenyl) (4-trifluoromethyl phenylamino) methyl] phosphonate 6g is characterized by single-crystal X-ray analysis. These compounds exhibited a strong antifungal effect, a low inhibition of AChE, and no inhibitory activity on BChE, with interesting antioxidant capacity. Results make them promising candidates as original organophosphorus pesticides. The DFT calculations concerning relative stability of various conformers, besides the comparison of the measured and calculated NMR spectra of selected compounds; suggest that conformational interconversion can quite easily occur in this type of molecules, so that many structures of the same compound can coexist in solution.
Exploration of α-aminophosphonate N-derivatives as novel, potent and selective inhibitors of protein tyrosine phosphatases
Wang, Qingming,Zhu, Miaoli,Zhu, Ruiting,Lu, Liping,Yuan, Caixia,Xing, Shu,Fu, Xueqi,Mei, Yuhua,Hang, Qingwei
experimental part, p. 354 - 364 (2012/04/23)
Seventeen α-aminophosphonates are synthesized. Their compositions and structures are established by EA, UV, FT-IR, 1H NMR, 13C NMR, 31P NMR and ESI-MS. Compounds 1-4 are confirmed by X-ray crystallography. PTP inhibition shows compounds 1-5, 12, 15 are moderate competitive inhibitors with some selectivity. The most potent inhibitor is compound 5 with the lowest IC50 value about 6.64 μM against PTP1B, about 2-fold and 25-fold stronger than against TCPTP and PTP-MEG2 while it doesn't inhibit SHP-1 and SHP-2. The binding constant of 5 to PTP1B is 2.23 × 105 M-1 and binding ratio approximates 1:1. Cell viability and apoptosis assays indicate 5 is cell permeable with lower cytotoxicity. The results indicate α-aminophosphonates are possibly developed to effective and selective inhibitors of PTPs.
