Ginkgolides: Selective acetylations, translactonization, and biological evaluation

被引:20
作者
Jaracz, S [1 ]
Stromgaard, K [1 ]
Nakanishi, K [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
D O I
10.1021/jo020139n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Protocols for selective acetylation of the hydroxyl groups of ginkgolide C have been developed. These acetylations have given rise to various ginkgolide C acetates and iso-ginkgolide C acetates, the latter having a rearranged skeleton resulting from translactonization. These acetyl derivatives, as well as ginkgolides A and B acetates have been investigated for their ability to bind to a cloned platelet-activating factor (PAF) receptor.
引用
收藏
页码:4623 / 4626
页数:4
相关论文
共 22 条
[1]   INTRAMOLECULAR AND INTERMOLECULAR HYDROXYL REACTIVITY DIFFERENCES IN GINKGOLIDE-A, GINKGOLIDE-B GINKGOLIDE-C AND THEIR CHEMICAL APPLICATIONS [J].
COREY, EJ ;
RAO, KS ;
GHOSH, AK .
TETRAHEDRON LETTERS, 1992, 33 (46) :6955-6958
[2]  
HASLER A, 2000, MED AROMATIC PLANTS, V12, P109
[3]   Chemistry of ginkgolides: structure-activity relationship as PAF antagonists [J].
Hu, LH ;
Chen, ZL ;
Cheng, XF ;
Xie, YY .
PURE AND APPLIED CHEMISTRY, 1999, 71 (06) :1153-1156
[4]   A simple photo-affinity labeling protocol [J].
Li, HY ;
Liu, Y ;
Fang, K ;
Nakanishi, K .
CHEMICAL COMMUNICATIONS, 1999, (04) :365-366
[5]  
MARUYAMA M, 1967, TETRAHEDRON LETT, P299, DOI 10.1016/S0040-4039(00)71538-3
[6]  
MARUYAMA M, 1967, TETRAHEDRON LETT, P315
[7]  
MARUYAMA M., 1967, TETRAHEDRON LETT, V4, P309
[8]  
MARUYAMA M., 1967, TETRAHEDRON LETT, V4, P303
[9]  
MARUYAMA M, 1969, UNPUB
[10]   STRUCTURE OF BILOBALIDE, A RARE TERT BUTYL CONTAINING SESQUITERPENOID RELATED TO C20-GINKGOLIDES [J].
NAKANISHI, K ;
HABAGUCHI, K ;
NAKADAIRA, Y ;
WOODS, MC ;
MARUYAMA, M ;
MAJOR, RT ;
ALAUDDIN, M ;
PATEL, AR ;
WEINGES, K ;
BAHR, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (14) :3544-+