Synthesis and biological activity of novel thiazolidin-4-ones with a carbohydrate moiety.
Some novel 2-aryl-3-[5-deoxy-1,2-O-isopropylidene-alpha-D-xylofuranose-5-C-yl] thiazolidin-4-ones were synthesized by the three-component condensation of an amino sugar 1, an aromatic aldehyde 2, and mercaptoacetic acid 3 in the presence of DCC and DMAP at room temperature. Two diastereoisomers 4 and 5 were afforded as the main products in totally isolated yields of 25.4-70%. The reaction was carried out with almost no observed stereoselectivity except in the case of 2c, which showed a moderate stereoselectivity. The structures of the new compounds were determined by NMR spectroscopy and mass spectrometry (MS), and the configuration of the newly generated chiral carbon (C-2) in the thiazolidin-4-one ring was tentatively assigned based on the X-ray crystallographic structure of 5d and the comparison of their corresponding NMR signals. The antitumor (human cervical cancer cells) activity and the inhibition against the glycosidases (alpha-glucosidase, beta-glucosidase, alpha-amylase) have been evaluated for the new compounds, some of which exhibited antitumor activity.
Chen
Hua
H
Department of Chemistry, Laboratory of Chemical Biology, Ministry of Education, Hebei University, Baoding, Hebei 071002, China.
Jiao
Lingling
L
Guo
Zaihong
Z
Li
Xiaoliu
X
Ba
Cuilan
C
Zhang
Jinchao
J
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002241:Carbohydrates / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D013843:Thiazines / Q000737:chemistry*
D000970:Antineoplastic Agents; D016227:Benzoquinones; D002241:Carbohydrates; D004791:Enzyme Inhibitors; D013843:Thiazines; D006026:Glycoside Hydrolases