An efficient synthesis of quinoxaline derivatives from 4-chloro-4-deoxy-alpha-D-galactose and their cytotoxic activities

作者：Yan Lin; Liu Feng Wu; Dai Gui Fu; Liu Hong Min^*

来源：Bioorganic & Medicinal Chemistry Letters, 2007, 17(3): 609-612.

DOI：10.1016/j.bmcl.2006.11.007

• 4-chloro-4-deoxy-alpha-D-galactose
• quinoxaline derivatives
• cytotoxicity

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)(2)O-Br-2 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.

• 出版日期2007-2-1
• 单位郑州大学