183963-69-1Relevant academic research and scientific papers
N-Propargyl-α-aminophosphonates in 1,3-Dipolar Cycloaddition with Azide-Containing Pharmacophores
Sokolov,Aksinenko, A. Yu.
, p. 1922 - 1926 (2018)
Some transformations of N-propargyl-α-aminophosphonates synthesized by the Kubachnik–Fields reaction were studied in copper-catalyzed 1,3-dipolar cycloaddition with azide-containing pharmacophores (phenothiazine, tetrahydrocarbazole, carbazole, and 3,5-dimethyl-1-aminoadamantane) leading to the formation of the corresponding 1,4-substituted 1,2,3-triazoles and allowing the introduction of a diethoxyphosphoryl fragment into the molecules of potential neuroprotectors.
Phosphatase inhibitors. III. Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase
Beers, Scott A.,Schwender, Charles F.,Loughney, Deborah A.,Malloy, Elizabeth,Demarest, Keith,Jordan, Jerold
, p. 1693 - 1701 (2007/10/03)
Further investigation of the structural requirements of a series of benzylphosphonic acid inhibitors of human prostatic acid phosphatase has led to the highly potent series of α-aminobenzylphosphonic acids. The α-benzylaminobenzylphosphonic acid, with an IC50 = 4 nM, exhibited a 3500-fold improvement in potency over the carbon analogue, α-phenylethyl. The enhanced potency may be due to a combination of four favorable interactions including those with the phosphate binding region, the presence the hydrophobic moieties of the benzylamino and phenylphosphonic acid, and a rigid conformer produced by an internal salt bridge between the phosphonate and the α-amino group. Replacement of the phosphonic acid moiety with a phosphinic or carboxylic acid as well as deletion of the benzyl substitution on the α-amino group led to great reductions in potency.
