Synthesis of novel phosphono peptidomimetics

Phosphonopeptides containing free phosphonic groups: recent advances

“…Availability of the latter ones opened an original route to structurally variable phosphonopeptides 35 and 36. [49][50][51][52][53] A preliminary study on the addition of thiols and amines to double bonds of quite readily affordable phosphono dehydropeptide 37 (Fig. 12) indicated that this procedure could be a new mean to produce phosphono peptides containing nontypical side chains (compounds 38 and 39).…”

Synthesis of novel phosphorylated peptidomimetics which contain ω-haloalkyl and ω-thiocyanoethyl residues

“…Minor products 3 and 4 could not be isolated in an individual state, but they can be obtained by other methods, which are described in paper. 18 Chloroalkyl products 2a-d are viscous colorless oils, poorly soluble in water and hexane, readily soluble in alcohols, benzene, methylene chloride, chloroform and dimethylsulfoxide. Their composition and structure are consistent with the data of elemental analysis, 1 Н, 13 С, and 31 Р NMR and IR spectroscopy, as well as chromatography-mass spectrometry.…”

“…Particular attention is drawn to the derivatives of 5-amino-1,3-oxazol-4-ylphosphonic acids, which under conditions of acidic cleavage form peptidomimetics containing the residues of phosphorylated glycine. [13][14][15][16][17][18][19] High biological activity of phosphorus-containing peptides is known. For example, selective inhibitors of cellular cymase, 20 glutathione transferase, 21,22 HCV NS3/NS4A serine protease, 23 vasoactive compounds, [24][25][26] etc., were found among these compounds.…”

“…It was previously shown that the 5-amino-1,3-oxazole derivatives containing the diethoxyphosphoryl group in position 4 are cleaved by water in the presence of various acidic agents such as acetic acid, 17,19 trifluoroacetic acid, 18,19 hydrochloric acid 34,35 and p-toluenesulfonic acid. 16 Also recently, we found that when diethyl ester (5-(2-hydroxyethyl)-N-methylamino)-2-phenyl-1,3-oxazol-4-ylphosphonic acid reacts with hydrogen chloride under anhydrous conditions, a phosphopeptidomimetic containing 2-chloroethyl fragment 18 is formed. The aim of the present work is to identify the scope of cleavage reaction of 4-phosphorylated 1,3-oxazole derivatives containing various aminoalkanol residues in position 5 in anhydrous medium in the presence of acidic reagents in order to obtain new phosphopeptidomimetics.…”

1,3-Oxazoles as precursors of phosphorylated amino acids and peptidomimetics

“…In order to obtain phosphonopeptidomimetics that are containe acyclic amino alcohol group, oxazoles 13 cleavage with trifluoroacetic acid was used. In this case, depending on the temperature of the reaction, it is possible to obtain esters 14a or acids 14b [22,23] (Scheme 4). Scheme 3.…”