Recent synthesis of aminophosphonic acids as potential biological importance

Abstract

Aminophosphonic acids are an important group of medicinal compounds, and their synthesis has been a focus of considerable attention in synthetic organic chemistry as well as medicinal chemistry. Although the phosphonic and carboxylic acid groups differ considerably with respect to shape, size, and acidity, alpha-aminophosphonic acids are considered to be structural analogues of the corresponding amino acids and the transition state mimics peptide hydrolysis. This review summarizes recent developments in the synthesis, characterization and biological activity of alpha-aminophosphonic acid and N-analogues. An account of both uses will be presented, emphasizing one of the potential future developments, and some implications in medicinal chemistry are also disclosed. In addition, a brief account on the characterization of N-(phosphonomethyl) glycine derivatives will be presented.

N–H···O=P hydrogen-bonded dimers as the main structural motif of aminophosphonate diesters

“…Phosphonate derivatives show a broad spectrum of chemically and biologically significant activities [1][2][3][4][5]. These compounds are widely used as broad-spectrum antiviral agents [6] and for treatment of bone diseases [7], while some complexes of platinum group metals exhibit remarkable antitumor activity [8][9][10][11].…”

Stereoselective Synthesis of α-Amino-C-phosphinic Acids and Derivatives

“…These classes of compounds are currently attracting great interest in organic and medicinal chemistry, as well as in agriculture, due to their important biological and pharmacological properties [1][2][3][4][5]. The great importance of this type of compounds has prompted organic chemists to report numerous procedures for their racemic or stereoselective synthesis [6][7][8][9][10][11].…”

Diethyl boronobenzylphosphonates as substrates in Petasis reaction

“…Frequently such efforts appeared successful and resulted in compounds of variable and promising physiological activity and in commercially available substances. [1][2][3][4][5] In addition, aminophosphonic acids and their derivatives are able to form complexes with a variety of metal ions. 6 These findings ensure that they still continue to attract wide interest.…”

“…5,[7][8][9][10] However, in most cases they give rise to compounds of relatively simple structure. Therefore, there is a strong need for elaboration of new synthetic procedures leading to functionalized aminophosphonates.…”