20369-41-9Relevant articles and documents
Benzyl Mono-P-Fluorophosphonate and Benzyl Penta-P-Fluorophosphate Anions Are Physiologically Stable Phosphotyrosine Mimetics and Inhibitors of Protein Tyrosine Phosphatases
Wagner, Stefan,Accorsi, Matteo,Rademann, J?rg
supporting information, p. 15387 - 15395 (2017/11/09)
α,α-Difluoro-benzyl phosphonates are currently the most popular class of phosphotyrosine mimetics. Structurally derived from the natural substrate phosphotyrosine, they constitute classical bioisosteres and have enabled the development of potent inhibitors of protein tyrosine phosphatases (PTP) and phosphotyrosine recognition sites such as SH2 domains. Being dianions bearing two negative charges, phosphonates, however, do not permeate membranes and thus are often inactive in cells and have not been a successful starting point toward therapeutics, yet. In this work, benzyl phosphonates were modified by replacing phosphorus-bound oxygen atoms with phosphorus-bound fluorine atoms. Surprisingly, mono-P-fluorophosphonates were fully stable under physiological conditions, thus enabling the investigation of their mode of action toward PTP. Three alternative scenarios were tested and mono-P-fluorophosphonates were identified as stable reversible PTP1B inhibitors, despite of the loss of one negative charge and the replacement of one oxygen atom as an H-bond donor by fluorine. In extending this replacement strategy, α,α-difluorobenzyl penta-P-fluorophosphates were synthesized and found to be novel phosphotyrosine mimetics with improved affinity to the phosphotyrosine binding site of PTP1B.
The first synthesis of diethyl α,α- chlorofluorobenzylphosphonates
Wu, Di,He, Yanhong,Tang, Rongchang,Guan, Zhi
supporting information; experimental part, p. 2180 - 2182 (2011/03/20)
Starting from a-hydroxyphosphonates, a wide variety of diethyl α,α-chlorofluorobenzylphosphonates have been obtained in pure form in a two-step procedure. The first step was chlorination of a- hydroxyphosphonates with Ph3P and CCl4,
Electrolytic partial fluorination of organic compounds 84. Anodic mono- and difluorination of benzylphosphonate derivatives
Zagipa, Bakenova,Hidaka, Asami,Cao, Yi,Fuchigami, Toshio
, p. 552 - 557 (2008/03/27)
Anodic fluorination of benzylphosphonate derivatives was carried out under various electrolytic conditions to provide the corresponding α-mono- and/or α,α-difluoro-products in moderate to good yields. It was found that the selectivity of fluorinated produ
