One-pot synthesis of phenylseleno N-acetyl α-amino acids: Supra-molecular self-assembling in organoselenium compounds

•One pot synthesis of phenylseleno N-acetyl α-amino acids is reported.•These compounds give supra-molecular self assembled structures.•Different amino acid fragment generate different motifs of secondary structures.•These compounds show free radical scavenging activity.

A convenient one-pot synthesis of phenylseleno N-acetyl α-amino acids, PhSeCH2C(O)NHC(R)COOH (R = H (1), Me (2), PhCH2 (3), 4-HOC6H4CH2 (4) and CH2OH (5)) is reported. These compounds have been characterized by microanalyses, UV–Vis, IR and NMR (1H, 13C, 77Se) spectroscopy. The molecular structures of [PhSeCH2CONHCH2COOH] (1), [PhSeCH2CONHCH(CH2C6H4OH-4)COOH] (4) and [PhSeCH2CONHCH(CH2OH)COOH] (5) have been established by X-ray diffraction analyses. These compounds are associated in the solid state through hydrogen bonding to give supra-molecular self-assembled structures. Free radical scavenging activity of these compounds has also been evaluated by DPPH assay.

Graphical abstractA one-pot synthesis of phenylseleno N-acetyl α-amino acids is reported. The molecular structures of [PhSeCH2CONHCH2COOH], [PhSeCH2CONHCH(CH2C6H4OH-4)COOH] and [PhSeCH2CONHCH(CH2OH)COOH] revealed association in the solid state through hydrogen bonding to give supra-molecular self-assembled structures. Free radical scavenging activity of these compounds has also been evaluated by DPPH assay.Figure optionsDownload full-size imageDownload as PowerPoint slide