Synthesis of furanosyl alpha-C-glycosides derived from 4-chloro-4-deoxy-alpha-D-galactose and their cytotoxic activities.
Condensation of a new unnatural sugar 1 with 1,3-dicarbonyl compounds in the presence of anhydrous zinc chloride gave the polyhydroxyalkyl-furans in excellent yields. Further modification afforded the corresponding furanosyl alpha-C-glycoside derivatives. The absolute configuration of 3-acetyl-2-methyl-5-(2'-chloro-D-galacto-tetritol-1-yl)-furan was confirmed by single-crystal X-ray analysis. The in vitro cytotoxic activities of these furanosyl C-glycosides were also investigated.
Yan
Lin
L
New Drug Research & Development Center, Zhengzhou University, Zhengzhou 450052, China.
Dai
Gui-Fu
GF
Yang
Jian-Li
JL
Liu
Feng-Wu
FW
Liu
Hong-Min
HM
D000230:Adenocarcinoma / Q000473:pathology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D045744:Cell Line, Tumor / Q000187:drug effects; D002712:Chlorides / Q000737:chemistry; D005643:Fucose / Q000031:analogs & derivatives* / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis / Q000494:pharmacology*; D006801:Humans; D008175:Lung Neoplasms / Q000473:pathology*; D009682:Magnetic Resonance Spectroscopy; D013329:Structure-Activity Relationship; D017967:Zinc Compounds / Q000737:chemistry
C411482:4-chloro-4-deoxygalactose; D000970:Antineoplastic Agents; D002712:Chlorides; D005663:Furans; D006027:Glycosides; D017967:Zinc Compounds; D005643:Fucose; C016837:zinc chloride