183964-34-3Relevant academic research and scientific papers
Direct transformation of amides into α-amino phosphonates via a reductive phosphination process
Gao, Yuzhen,Huang, Zhongbin,Zhuang, Rongqiang,Xu, Jian,Zhang, Pengbo,Tang, Guo,Zhao, Yufen
supporting information, p. 4214 - 4217 (2013/09/12)
The first general method for the reductive phosphination of amides in one pot has been developed. The reactions described provide a novel access to α-amino phosphonates in good to excellent yields, cover a broad scope of substrates such as secondary and tertiary amides, and do not require a low temperature.
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.
