173039-08-2Relevant articles and documents
Mechanism of Phosphorus-Carbon Bond Formation in the Amidoalkylation of Phosphonous Carboxylic Acids
Dmitriev, Maxim E.,Golovash, Sofia R.,Borodachev, Alexei V.,Ragulin, Valery V.
supporting information, p. 593 - 600 (2021/01/14)
An unusual greater reactivity of phosphonous propionic acids was found in comparison with phosphonous propionic esters in carbamate version of Kabachnik-Fields reaction. Compounds of tricoordinated phosphorus generated in situ during the amidoalkylation o
Compounds and inhibitors of phospholipases
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, (2008/06/13)
The present invention relates generally to amino acid derivatives and to methods of making the same. In particular, the invention relates to compounds bearing a stereochemical identity, that is, the same stereochemistry, with the chiral α-carbon of D-α-amino acids and their use in methods of therapy, including the treatment of inflammatory diseases, and to compositions and enantiomeric mixtures containing them.
Phosphinic acid pseudopeptides analogous to glutamyl-γ-glutamate: Synthesis and coupling to pteroyl azides leads to potent inhibitors of folylpoly-γ-glutamate synthetase
Valiaeva,Bartley,Konno,Coward
, p. 5146 - 5154 (2007/10/03)
Several routes to a complex phosphinate phosphapeptide analogous to the γ-glutamyl peptide Gluγ-Glu have been investigated. Formation of γ-phosphono glutamate derivatives via addition of a phosphorus-based radical to protected vinylglycine was found to be of limited value because of the elevated temperatures required. Alkylation and conjugate addition reactions of trivalent phosphorus (PIII) species were investigated. In situ generation of bis-trimethylsilyl esters of phosphinous acids proved to be an effective route to phosphinates of modest structural complexity. However, this chemistry could not be extended to the incorporation of an amino acid moiety at the N-terminal side of the desired phosphinate. A successful synthesis of the target phosphinate phosphapeptide was effected using PIII chemistry and dehydrohalogenation to yield an α,β-unsaturated phosphinic acid ester, following which conjugate addition of diethylacetamido malonate and acid-mediated hydrolysis afforded the desired phosphinate phosphapeptide. Coupling of the unprotected phosphinate phosphapeptide with two acyl azides derived from folic acid and methotrexate led to the corresponding pteroylphosphapeptides of interest as possible mimics of tetrahedral intermediates in the reaction catalyzed by folylpolyglutamate synthetase.
Design, synthesis, and biological activity of a potent inhibitor of the neuropeptidase N-acetylated alpha-linked acidic dipeptidase.
Jackson, Paul F.,Cole, Derek C.,Slusher, Barbara S.,Stetz, Susan L.,Ross, Laurie E.,et al.
, p. 619 - 622 (2007/10/03)
A series of substituted phosphonate derivatives were designed and synthesized in order to study the ability of these compounds to inhibit the neuropeptidase N-acetylated alpha-linked acidic dipeptidase (NAALADase). The molecules were shown to act as inhib
