Stereoselectivity of binding of α-(N-benzylamino)benzylphosphonic acids to prostatic acid phosphatase

Synthesis and Evaluation of 1-Aryl-1-(7-carboxy-isoindolin-1-one-2-yl)methylphosphonic Acid Derivatives as Inhibitors of Protein Tyrosine Phosphatase

“…We expected that phosphorylated isoindolin-1-one derivatives 1 could have additional effects acting as structural analogues of natural organic phosphates in biochemical transformations catalyzed by various phosphatases. 2 Isoindolin-1-one phosphonic acids 1 (Figure 1), as the first aims of this work, were synthesized by dehydrative aromatization of (2,3,7,7a-tetrahydro-3a,6-epoxyisoindolin-1-one)phosphonates, which have been obtained by tandem acylation/[4+2]-cycloaddition between furfurylaminophosphonates and maleic anhydride. 1 The potential of inhibitors of protein tyrosine phosphatases with two or more anionic groups prompted us to synthesize a series of new derivatives of isoindolin-1-one-2-ylmethylphosphonic acids bearing a benzamide substituent with NO 2 , COOH, or COCOOH groups (compounds 2).…”

Fourier Transform Infrared and Raman and Surface-Enhanced Raman Spectroscopy Studies of a Novel Group of Boron Analogues of Aminophosphonic Acids

“…6,7 Modifying aminophosphonic acids to (N-benzylamino)-benzylphosphonic acids produces the most effective phosphatase inhibitors; phosphatase is an enzyme that catalyzes the dephosphorylation process. 8,9 Additional introduction of a boronic acid group to the biologically active (N-benzylamino)-benzylphosphonic acid opens new possibilities for its application. Boronic acid compounds have attracted recent attention because of their biomedical functions: they are used as potential diol 10 and saccharide receptors 11−13 and as enzyme inhibitors.…”

Facile synthesis of α‐amino phosphonates in water by Kabachnik–Fields reaction using magnesium dodecyl sulfate

“…The synthesis of α-amino phosphonates has attracted much attention due to their significant biological activities such as antibacterial and anti-HIV, structural analogy to α-amino acids, and transition state mimics of peptide hydrolysis [1,2]. Nucleophilic addition reaction of phosphites to imines is one of the most preferred methods [3].…”