摘要
目的:合成匹诺塞林的两种体内代谢产物5-羟基-黄烷酮-7-O-磺酸钠及5-羟基-黄烷酮-7-O-β-D-葡糖糖醛酸。方法:以匹诺塞林为原料,吡啶作为溶剂和催化剂,与氯磺酸进行磺酸化反应后再成盐得到5-羟基-黄烷酮-7-O-磺酸钠。5-羟基-黄烷酮-7-O-β-D-葡糖糖醛酸的合成同样以匹诺塞林为原料,经过乙酰化保护羟基,再选择性脱去保护基,然后与三-O-乙酰基-α-D-溴代葡糖糖醛酸甲酯进行糖苷化,再水解脱去保护基团得到目标化合物。结果:两个目标化合物的结构经1H-NMR、MS得到确证,纯度经HPLC检测均达到98%以上。结论:本文首次合成了5-羟基-黄烷酮-7-O-磺酸钠和5-羟基-黄烷酮-7-O-β-D-葡糖糖醛酸两种代谢产物,可作为新药匹诺塞林体内代谢研究的对照品。
Objective： To synthesize two metabolites of pinocembrin, 5-hydroxy-flavanone-7-O-sodium sul- phonate and 5-hydroxy-flavanone-7-O-β-D-glucuronic acid none-7-O-sodium sulphonate was synthesized by sulfonating Methods ： Starting from pinocembrin, 5-hydroxy-flava- with chlorosulfonic acid using pyridine as the solvent and catalyst. 5-Hydroxy-flavanone-7-O-β-D-glucuronic acid was also synthesized from pinocembrin by acetyl pro- tection, selective deprotection, glycosidation with methyl （tri-O-acetyl-α-D-gluco-pyranosyl bromide ） -urinate and removal of the protection groups. Results： The structures of the two objective compounds were confirmed by 1H-NMR and MS, and their purities were over 98% as determined by HPLC. Conclusion： Two metabolites of pi- nocembrin, 5-hydroxy-flavanone-7-O-β-D-glucuronic acid and 5-hydroxy-flavanone-7-O-sodium sulphonate, were synthesized for the first time, and they can be used as the reference substances in the metabolic studies of pinocem- brin in vivo.
出处
《中国新药杂志》
CAS
CSCD
北大核心
2013年第10期1130-1132,1165,共4页
Chinese Journal of New Drugs
基金
国家"重大新药创制"科技重大专项(2012ZX09301002-001)
