87750-65-0Relevant academic research and scientific papers
SAR of non-hydrolysable analogs of pyridoxal 5′-phosphate against low molecular weight protein tyrosine phosphatase isoforms
DeSouza, Shirin R.,Flynn, Rebecca S.,Jakubowski, Henry V.,Marshall, Quinlen F.,McIntee, Edward J.,Olson, Maxwell C.,Sinner, Erica K.,Tinucci, Samantha L.
supporting information, (2020/07/21)
Kinases and phosphatases are key enzymes in cell signal transduction pathways. Imbalances in these enzymes have been linked to numerous disease states ranging from cancer to diabetes to autoimmune disorders. The two isoforms (IFA and IFB) of Low Molecular Weight Protein Tyrosine Phosphatase (LMW-PTP) appear to play a role in these diseases. Pyridoxal 5′-phosphate (PLP) has been shown to act as a potent but, impractical micromolar inhibitor for both isoforms. In this study, a series of non-hydrolysable phosphonate analogs of PLP were designed, synthesized and tested against the two isoforms of LMW-PTP. Assay results demonstrated that the best inhibitor for both isoforms was compound 5 with a Kis of 1.84 μM (IFA) and 15.6 μM (IFB). The most selective inhibitor was compound 16, with a selectivity of roughly 370-fold for IFA over IFB.
Cu(i)/Fe(III)-Catalyzed C-P cross-coupling of styrenes with H-phosphine oxides: A facile and selective synthesis of alkenylphosphine oxides and β-ketophosphonates
Gu, Jian,Cai, Chun
supporting information, p. 4226 - 4230 (2017/07/10)
Cu(i)/Fe(iii)-Catalyzed phosphorylation and oxyphosphorylation of styrenes with H-phosphonates which can be controlled by varying the reaction temperature are developed. This study offers a new and expedient strategy for the synthesis of useful alkenylphosphine oxides and β-ketophosphonates in satisfactory yields. Moreover, the transformation is proposed to proceed via a radical process and exhibits a broad substrate scope and good functional group tolerance.
A (E) - 2-aryl ethylene cinnamenyl method for preparing ester derivative
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Paragraph 0056-0058, (2017/03/08)
The invention discloses method for preparing (E)-2-aryl vinyl phosphonate derivatives. The method comprises the specific following steps of dissolving 1-nitro-2-aryl-vinyl derivatives, a phosphorus reagent, an accelerator manganese acetate and a catalyst copper acetate in a solvent and reacting at 20-100 DEG C to obtain the (E)-2-aryl vinyl phosphonate derivatives. According to the method disclosed by the invention, the 1-nitro-2-aryl-vinyl derivatives are adopted as starting materials, the raw materials are easily available and have multiple varieties; the products obtained by the method disclosed by the invention are multiple and can be directly applied and can be also used for other further reaction; according to the method, the use of precious metal reagents and other additives is avoided; and meanwhile, the synthetic route is short, reaction conditions are mild, the reaction operation and post-treatment process are simple, the yield is high and the method is suitable for scale production.
Silver-catalyzed synthesis of 2-arylvinylphosphonates by cross-coupling of β-nitrostyrenes with: H -phosphites
Yuan, Jin-Wei,Yang, Liang-Ru,Mao, Pu,Qu, Ling-Bo
, p. 87058 - 87065 (2016/09/23)
An efficient protocol for stereoselective synthesis of 2-arylvinylphosphonates has been developed via AgNO3-catalyzed cross-coupling of β-nitrostyrenes with dialkyl H-phosphites under mild conditions. By losing the nitro group of β-nitrostyrene
Stereoselective synthesis of vinylphosphonates and phosphine oxides via silver-catalyzed phosphorylation of styrenes
Gui, Qingwen,Hu, Liang,Chen, Xiang,Liu, Jidan,Tan, Ze
supporting information, p. 13922 - 13924 (2015/09/07)
An efficient and stereoselective synthesis of vinylphosphonates and phosphine oxides was developed starting from styrenes using AgNO3 as the catalyst and K2S2O8 as the oxidant. The success of the reaction was fo
Manganese(iii)-mediated alkenyl Csp2-P bond formation from the reaction of β-nitrostyrenes with dialkyl phosphites
Xue, Jian-Fei,Zhou, Shao-Fang,Liu, Ye-Ye,Pan, Xiangqiang,Zou, Jian-Ping,Asekun, Olayinka Taiwo
, p. 4896 - 4902 (2015/05/05)
Mn(OAc)3-mediated tandem phosphonyl radical addition to β-nitrostyrenes followed by denitration to form (E)-2-alkenyl phosphonates in good yield is described.
Synthesis of diethyl 2-(aryl)vinylphosphonate by the Heck reaction catalysed by supported palladium catalysts
Tarabay, Jinane,Al-Maksoud, Walid,Jaber, Farouk,Pinel, Catherine,Prakash, Swamy,Djakovitch, Laurent
experimental part, p. 124 - 133 (2011/02/23)
The synthesis of diethyl 2-(aryl)vinylphosphonate through direct Heck coupling reaction of the diethyl vinylphosphonate with aryl or heteroaryl halides catalysed by solid materials ([Pd(NH3)4]/NaY, Pd/C, PdO/SiO2) is reported. After optimising the reaction conditions (1.3 mol% [Pd(NH3)4]/NaY, DMF, K2CO 3, 110-140 °C), various aryl and heteroaryl halides were engaged in this reaction leading in all cases good to high yields. Interestingly, when using activated aryl bromides the palladium loading could be lowered to only 0.25 mol%. While highly active when coupling aryl iodides (i.e. only 0.15 mol% required), the PdO/SiO2 catalyst was found to be inactive when considering aryl bromides. Deep study of this catalytic material revealed that in the case of aryl bromides, absence of in situ reduction of the catalyst precursor prevents the cross-coupling reaction with this latter material.
Synthesis of diethyl 2-(aryl)vinylphosphonates by the Heck reaction catalysed by well-defined palladium complexes
Al-Maksoud, Walid,Mesnager, Julien,Jaber, Farouk,Pinel, Catherine,Djakovitch, Laurent
experimental part, p. 3222 - 3231 (2010/01/11)
Pd-catalysed procedures for the direct Heck arylation of diethyl vinylphosphonate with various aryl or heteroaryl halides toward the synthesis of diethyl 2-(aryl)vinylphosphonates are reported. Several homogeneous catalytic systems (i.e. Herrmann palladacycle, Nolan (NHC)-palladium catalyst, Pd(OAc)2/PPh3) were used and compared within the study. High conversions and selectivities were achieved under optimised conditions (2 mol% [Pd], NMP, K2CO3, 140 °C) whatever the homogeneous catalyst used.
Metallo-phosphorylation of alkenes: a highly regioselective reaction of zirconocene-alkene complexes with chlorophosphate
Lai, Chunbo,Xi, Chanjuan,Chen, Weixuan,Hua, Ruimao
, p. 6295 - 6302 (2007/10/03)
Zirconocene-alkene complexes Cp2Zr(CH2{double bond, long}CHR) reacted with chlorophosphate to form zircono-ethylphosphonate with high regioselectivity, which is versatile and could be converted into various functionalized organophosphonates.
Knoevenagel reaction of diethylphosphonoacetic acid: A facile route to diethyl (E)-2-arylvinylphosphonates
Krawczyk, Henryk,Albrecht, Lukasz
, p. 2887 - 2896 (2007/10/03)
Knoevenagel reaction of aromatic aldehydes or α-substituted aliphatic aldehydes with diethylphosphonoacetic acid leads to the formation of 3-substituted-2-(diethoxyphosphoryl)acrylic acids. Decarboxylation of the resulting (E)-3-aryl-2-(diethoxyphosphoryl)acrylic acids afforded diethyl (E)-2-arylvinylphosphonates. Direct synthesis of diethyl vinylphosphonates from some aromatic aldehydes and formaldehyde is also reported. Georg Thieme Verlag Stuttgart.
