Synthesis and anti-tumor activities of methyl 2-O-aryl-6-O-aryl'-D-glucopyranosides.
A synthetic method of introducing bulky aryl groups at the 2-O- and 6-O-positions on glucopyranosides was developed. A total of 37 new compounds of this class were obtained successfully. These compounds were tested on several tumor cell lines by MTT assays, and some of them exhibited encouraging inhibitory activities. The most potent compound, CAB-SHZH-27, exhibited EC(50) values of 14, 12, and 10 micromol/L on A549, MDA-MB-231 and HeLa cells, respectively. A preliminary structure-activity relationship analysis indicates that the two free hydroxyl groups on the D-glucose core are indispensable for the biological activities of this class of compounds, and the aryl group at the 6-O-position has a more obvious impact than the one at the 2-O-position. An interesting 'on-off' mechanism of this class of compounds was also observed in our MTT assays, which remains to be explored.
Shi
Hefang
H
Key Laboratory of Marine Drugs, The Ministry of Education of China, Marine Drug and Food Institute, Ocean University of China, Qingdao 266003, PR China.
Zhou
Bingcheng
B
Li
Wenwen
W
Shi
Zhimin
Z
Yu
Biao
B
Wang
Renxiao
R
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D006367:HeLa Cells; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy*; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D005960:Glucosides