Simple and efficient synthesis of novel glycosyl thiourea derivatives as potential antitumor agents.
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 76.4 microM and from 54.9 to 82.4 microM, respectively. And the other compounds did not demonstrate any significant cytotoxicity even at concentrations up to 200muM.
Shusheng
Zhang
Z
Key Laboratory of Eco-chemical Engineering, Ministry of Education, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Zhengzhou Road No. 53, Qingdao 266042, Shandong, PR China.
Tianrong
Zhan
Z
Kun
Cheng
C
Youfeng
Xia
X
Bo
Yang
Y
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D009369:Neoplasms / Q000188:drug therapy / Q000473:pathology*; D013237:Stereoisomerism; D013890:Thiourea / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D009005:Monosaccharides; D013890:Thiourea