125553-06-2Relevant academic research and scientific papers
Substituted phosphonic analogues of phenylglycine as inhibitors of phenylalanine ammonia lyase from potatoes
Wanat, Weronika,Talma, Micha?,Hurek, Józef,Pawe?czak, Ma?gorzata,Kafarski, Pawe?
, p. 119 - 127 (2018/06/14)
A series of phosphonic acid analogues of phenylglycine variously substituted in phenyl ring have been synthesized and evaluated for their inhibitory activity towards potato L-phenylalanine ammonia lyase. Most of the compounds appeared to act as moderate (
Sigmatropic isomerizations in azaallyl systems: XX. N- Alkylbenzimidoylphosphonates
Onys'ko,Kim,Rassukanaya,Kiseleva,Sinitsa
, p. 1341 - 1349 (2007/10/03)
Synthetic approaches are developed to benzimidoylphosphoryl derivatives containing electronically and sterically diverse alkyl substituents on the nitrogen atom, as well as their prototropic isomers. Regularities in prototropic transitions in the phosphorylated C=N-C triad were revealed and applied in the synthesis of α-aminophosphonic acid derivatives. 2004 MAIK "Nauka/Interperiodica".
Inhibitors of phenylalanine ammonialyase: 1-aminobenzylphosphonic acids substituted in the benzene ring
Zoń, Jerzy,Amrhein, Nikolaus,Gancarz, Roman
, p. 9 - 21 (2007/10/03)
Dextrorotatory 1-amino-3′,4′-dichlorobenzylphosphonic acid was found to be a potent inhibitor of the plant enzyme phenylalanine ammonia-lyase both in vitro and in vivo from among the ring-substituted 1-aminobenzylphosphonic acids and other analogues of phenylglycine. A structure activity relationship analysis of the results obtained permits predictions on the geometry of the pocket of the enzyme and is a basis in the strategy of better inhibitor synthesis.
The preparation and characterization of some fluorinated α-aminoarylmethanephosphonic acids
Green, Donovan St C.,Gruss, Ulrike,Haegele, Gerhard,Hudson, Harry R.,Lindblom, Lars,Pianka, Max
, p. 179 - 207 (2007/10/03)
α-Aminoarylmethanephosphonic acids have been prepared with a range of fluoro, fluoroalkyl, or fluoroalkoxy substituents in the benzene ring (4-F, 3-F, 2-F, 3,4-F2, F5, 4-CF3, 3-CF3, 4-CF3O, and 3-CF3O). These compounds have relatively low aqueous solubility and their NMR spectra (1H, 13C, 31P and 19F) were therefore recorded in D2O in the presence of an excess of alkali. Under these conditions, the ring substituents appear to have little effect on δp (15-18 ppm), or on the 1H and 13C parameters for the benzylic group (α-CH), which are mainly in the ranges observed for other types of α-aminoarylmethanephosphonic acids under alkaline conditions (δH 3.8-4.0 ppm, 2JPH 15.3-16.5 Hz; δC 57-58 ppm, 1JPC 128-132 Hz). For those examples with fluorine in the ortho position (i.e., the 2-fluoro and pentafluoro derivatives) a slightly higher field chemical shift was observed for the benzylic carbon atom (δC 50-51 ppm). In the fast-atom bombardment mass spectra, pseudo-molecular ions, MH+, and ions resulting from the elimination of phosphorous acid [MH - H3PO3]+, provide a further useful means of chararacterization for these compounds. Key words: Fluorinated aminoarylmethanephosphonic acids, dialkyl N-diphenylmethylaminoaryl-methanephosphonates, NMR spectroscopy, FAB mass spectrometry.
ORGANIC PHOSPHORUS COMPOUNDS 94 PREPARATION, PHYSICAL AND BIOLOGICAL PROPERTIES OF AMINO-ARYLMETHYLPHOSPHONIC- AND -PHOSPHONOUS ACIDS
Maier, Ludwig,Diel, Peter J.
, p. 57 - 64 (2007/10/02)
The preparation, physical and spectroscopic properties of amino-arylmethylphosphonic- and -phosphonous acids, the phosphorus analogues of phenylglycine, are described.It is shown that several of the compounds prepared exhibit antifungal activity at 200 ppm.Thus 1e, 1f, 1g and 1h showed activity against Erysiphe (barley), 2a against Puccinia (wheat) and 6a against Botrytis (apple).Of particular interest is the high gameticidal activity of 3a in the greenhouse.
