An efficient synthesis of quinoxaline derivatives from 4-chloro-4-deoxy-alpha-D-galactose and their cytotoxic activities.
A novel and efficient method for the synthesis of quinoxaline derivatives has been developed. Isopropylidenation of 4-chloro-4-deoxy-alpha-D-galactose with 2,2-dimethoxypropane, followed by selective hydrolysis, afforded 2,3-O-isopropylidene-4-chloro-4-deoxy-D-galactose di-methyl acetal (3) as a sole product. Oxidation of compound 3 with (Bu3Sn)2O-Br2 gave corresponding hex-5-ulose derivative in high yields. The hex-5-ulose derivative reacted with o-phenylenediamines under neutral conditions to afford quinoxaline derivatives in reasonable yields. The in vitro cytotoxic activities of these quinoxaline derivatives were investigated.
Yan
Lin
L
New Drug Research and Development Center, Zhengzhou University, Zhengzhou 450052, PR China.
Liu
Feng-Wu
FW
Dai
Gui-Fu
GF
Liu
Hong-Min
HM
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002241:Carbohydrates / Q000737:chemistry; D045744:Cell Line, Tumor; D005643:Fucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D013778:Tetrazolium Salts; D013844:Thiazoles
C411482:4-chloro-4-deoxygalactose; D000970:Antineoplastic Agents; D002241:Carbohydrates; D007202:Indicators and Reagents; D011810:Quinoxalines; D013778:Tetrazolium Salts; D013844:Thiazoles; D005643:Fucose; C022616:thiazolyl blue