Synthesis and in vitro study of pseudo-peptide thioureas containing α-aminophosphonate moiety as potential antitumor agents

Twenty pseudo-peptide thioureas IIa-1 containing alpha-aminophosphonate moiety were synthesized from the reaction of chiral alpha-amino carboxamide derivatives Ia-c with O,O '-dialkylisothiocyanato(phenyl) methylphosphonate 5. The synthesized compounds were completely characterized by elemental analysis, physical and spectral (IR, H-1 NMR, C-13 NMR) data. According to the preliminary studies on antitumor activities, compounds IIa-1 could inhibit tumor cells PD, Bcap37 and BGC823. These compounds displayed low to high activity by MTT assays. Among them, L-Ilk, D-IIa and D-IIe were identified as potent inhibitors, with IC50 values ranging from 4.7 to 11.2 mu M according to in vitro assay. (C) 2010 Elsevier Masson SAS. All rights reserved.