Simple and efficient synthesis of novel glycosyl thiourea derivatives as potential antitumor agents.

摘要

The practical synthesis of pseudonucleosides incorporating thiourea derivative by coupling of monosaccharides (d-galactose, d-glucose and d-xylose) per-O-acetylated glycosyl isothiocyanates and different heterocyclic hydrazide derivatives is reported. The method involves the preparation of per-O-acetylated glycosyl isothiocyanates from per-O-acetylated sugars (two-step synthesis), which couple with heterocyclic hydrazides from amines to give thiourea-linked pseudonucleosides. All newly synthesized pseudonucleosides were assayed against human lung cancer-cell lines (PG) and human liver cancer-cell lines (BEL-7402) in vitro. The 2-(4-methoxybenzamide)-benzoimidazole-1-yl-acetyl pseudonucleosides showed moderate inhibition against these two cancer-cell lines with EC(50) from 22.8 to 76.4muM and from 54.9 to 82.4muM, respectively. And the other compounds did not demonstrate any significant cytotoxicity even at concentrations up to 200muM.