1315481-74-3Relevant academic research and scientific papers
Copper-Catalyzed Microwave-Expedited Oxyphosphorylation of Alkynes with Diethyl Phosphite and t-Butyl Hydroperoxide Synthesis of Densely Functionalized Phosphonylated Indenones
Maciás-Benítez, Pablo,Sierra-Padilla, Alfonso,Tenorio, Manuel J.,Moreno-Dorado, F. Javier,Guerra, Francisco M.
, p. 16409 - 16424 (2021/11/16)
Treatment of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)4]BF4 under microwave irradiation produced the oxyphosphorylation of the triple bond, giving rise to the corresponding β-ketophosphonates in moderate-to-good yields. When the triple bond was conjugated to a carbonyl group bearing an aromatic ring, it led to the cyclization of the resulting ketone intermediate, producing eventually different phosphonylated indenones.
Copper-catalyzed decarboxylative C?P cross coupling of arylpropiolic acids with dialkyl hydrazinylphosphonates leading to alkynylphosphonates
Chen, Weizhu,Ma, Dumei,Hu, Gaobo,Hong, Zhuan,Gao, Yuxing,Zhao, Yufen
supporting information, p. 1175 - 1181 (2016/08/05)
A facile and novel copper-catalyzed decarboxylative coupling of various arylpropiolic acids with readily available dialkyl hydrazinylphosphonates has been developed, providing an attractive synthetic tool for the synthesis of valuable alkynylphosphonates
Design, synthesis and P-gp induction activity of aryl phosphonate esters: Identification of tetraethyl-2-phenylethene-1,1-diyldiphosphonate as an orally bioavailable P-gp inducer
Manda, Sudhakar,Wani, Abubakar,Bharate, Sonali S.,Vishwakarma, Ram A.,Kumar, Ajay,Bharate, Sandip B.
supporting information, p. 1910 - 1915 (2016/10/22)
The clearance of amyloid-beta is mediated by the P-glycoprotein (P-gp) transporter pump located at the blood brain barrier. Therefore, the induction of P-gp has been considered as a potential therapeutic strategy for the treatment of Alzheimer's disease. The expression of P-gp is regulated through a nuclear receptor, pregnane X receptor (PXR). Thus, herein we investigated the potential of a known PXR activator, diphosphonate ester SR12813 (6a), for P-gp induction activity and further studied its structure-activity relationship. The diphosphonate ester SR12813 along with three series of analogs, viz. aryl alkylidene, aryl alkynyl, and aryl α-amino phosphonate esters, were synthesized and screened for P-gp induction activity in P-gp overexpressing adenocarcinoma LS180 cells using rhodamine 123 efflux assay. The parent compound SR12813 along with several new analogs displayed P-gp induction activity at 5 μM. Western blot analysis indicated that tetraethyl-2-phenylethene-1,1-diyldiphosphonate (6c) and tetraethyl-2-(anthracene-10-yl)ethene-1,1-diyldiphosphonate (6s) showed 7-8-fold increase in P-gp expression in LS180 cells. The diphosphonate ester 6c displayed excellent aqueous solubility, no cytochrome P450 inhibition liability and no efflux pump substrate liability. Furthermore, it exhibits an excellent oral pharmacokinetic profile in BALB/c mice with AUC0-∞ of 2067 ng h mL-1 and 37.6% oral bioavailability. The results presented here clearly indicate the potential of this scaffold to increase the clearance of brain Aβ across the BBB and thus its promise for development as a potential anti-Alzheimer agent.
Cs2CO3-promoted one-pot synthesis of alkynylphosphonates, -phosphinates, and -phosphine oxides
Wang, Yulei,Gan, Jiepeng,Liu, Liu Leo,Yuan, Hang,Gao, Yuxing,Liu, Yan,Zhao, Yufen
, p. 3678 - 3683 (2014/05/06)
A novel and efficient Cs2CO3-promoted phosphorylation or phosphinylation of various 1,1-dibromo-1-alkenes with readily available trialkyl phosphites, ethyl diphenylphosphinite, or diethyl phenylphosphonite has been developed under metal-free conditions, providing a practical and powerful tool for one-pot synthesis of valuable alkynylphosphonates, -phosphinates, and -phosphine oxides in good to excellent yields.
