GP-7
2(3H)-硫代酰苯,3-乙基二氢-3-(1-甲基乙基)-(9CI)Chemical Name: 4-(2,2,6,6-Tetramethyl-1-oxylpiperidin-4-ylamino)-4'-demethylepipodophyllotoxin; 5alpha-(4-Hydroxy-3,5-dimethoxyphenyl)-9beta-(2,2,6,6-tetramethyl-1-oxylpiperidin-4-ylamino)-5,5abeta,6,8,8aalpha,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
CAS No. 125670-69-1
项目整合开发状态: Preclinical
项目研究机构: Lanzhou University (Originator)
合成路线:Podophyllotoxin (I),isolated from the roots of Podophyllum emodi Wall var.chinensis sprague by extraction with ethanol and purified through repeated recrystallization from ethanol-benzene,is demethylated and brominated in a single step.(I) is suspended in a cold mixture of ethylene dichloride and ether.Anhydrous hydrogen bromide is passed until the calculated weight increase is reached.After standing at 0-2 C for 20 hours,the solvent is removed under reduced pressure.4-Bromo-4-deoxy-4'-demethylepipodophyllotoxin (II) is recrystallized from acetone.A solution of (II) and 4-amino-2,2,6,6-tetramethylpiperidin-1-oxyl (III) with a trace of anhydrous pyridine in THF is refluxed under nitrogen atmosphere for 4 hours.The insoluble solid is removed by filtration and the solvent is distilled off under reduced pressure.The crude product is chromatographed twice through silica gel,using methylene chloride-acetone-diethylamine (40:1:1,by volume) as eluent.GP-7 is recrystallized from acetone-hexane.
📌 参考资料/链接：
参考文献标题:Anticancer drugs II.Synthesis and biological evaluation of spin labeled derivatives of podophyllotoxin
文献作者:Chen,Y.; Wang,Y.; Li,J.; Tian,X.; Jia,Z.; Zhang,P.
参考来源:Life Sci 1989,45(26),2569-75
📄 详细内容
合成路线:Podophyllotoxin (I),isolated from the roots of Podophyllum emodi Wall var.chinensis sprague by extraction with ethanol and purified through repeated recrystallization from ethanol-benzene,is demethylated and brominated in a single step.(I) is suspended in a cold mixture of ethylene dichloride and ether.Anhydrous hydrogen bromide is passed until the calculated weight increase is reached.After standing at 0-2 C for 20 hours,the solvent is removed under reduced pressure.4-Bromo-4-deoxy-4'-demethylepipodophyllotoxin (II) is recrystallized from acetone.A solution of (II) and 4-amino-2,2,6,6-tetramethylpiperidin-1-oxyl (III) with a trace of anhydrous pyridine in THF is refluxed under nitrogen atmosphere for 4 hours.The insoluble solid is removed by filtration and the solvent is distilled off under reduced pressure.The crude product is chromatographed twice through silica gel,using methylene chloride-acetone-diethylamine (40:1:1,by volume) as eluent.GP-7 is recrystallized from acetone-hexane.
参考文献标题:GP-7
文献作者:Ruyun,J.
参考来源:Drugs Fut 1992,17(3),191
合成路线:Podophyllotoxin (I),isolated from the roots of Podophyllum emodi Wall var.chinensis sprague by extraction with ethanol and purified through repeated recrystallization from ethanol-benzene,is demethylated and brominated in a single step.(I) is suspended in a cold mixture of ethylene dichloride and ether.Anhydrous hydrogen bromide is passed until the calculated weight increase is reached.After standing at 0-2 C for 20 hours,the solvent is removed under reduced pressure.4-Bromo-4-deoxy-4'-demethylepipodophyllotoxin (II) is recrystallized from acetone.A solution of (II) and 4-amino-2,2,6,6-tetramethylpiperidin-1-oxyl (III) with a trace of anhydrous pyridine in THF is refluxed under nitrogen atmosphere for 4 hours.The insoluble solid is removed by filtration and the solvent is distilled off under reduced pressure.The crude product is chromatographed twice through silica gel,using methylene chloride-acetone-diethylamine (40:1:1,by volume) as eluent.GP-7 is recrystallized from acetone-hexane.
参考文献标题:Spin-labeled antitumor derivatives of podophyllotoxin
文献作者:Chen,Y.; Tian,X.; Zhang,C.
参考来源:Scientia Sin 1987,30-B1070-9
产品链接: CAS No. 125670-69-1››