On the relationship of OSW-1 to the cephalostatins

被引:71
作者
Guo, CX [1 ]
LaCour, TG [1 ]
Fuchs, PL [1 ]
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
关键词
D O I
10.1016/S0960-894X(98)00743-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Antineoplastic bis-steroidal (cephalostatin-type) analogues of the saponin OSW-1 were produced from a dihydroaglycone of OSW-1. The key aglycone 6H was obtained from 5 alpha-androstan-3 beta-ol-17-one in 8 steps (38% yield). The SAR of the aglycones, intermediates, and hybrid analogues provide insights regarding the proposed common role of C22-oxocarbenium ions in the bioactivity of both OSW-1 and cephalostatins (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:419 / 424
页数:6
相关论文
共 15 条
[1]  
ALLEY MC, 1988, CANCER RES, V48, P589
[2]   MYELIN MEMBRANE STRUCTURE AT 10 A RESOLUTION [J].
CASPAR, DLD ;
KIRSCHNER, DA .
NATURE-NEW BIOLOGY, 1971, 231 (19) :46-+
[3]   Isolation of 13 new ritterazines from the tunicate Ritterella tokioka and chemical transformation of ritterazine B [J].
Fukuzawa, S ;
Matsunaga, S ;
Fusetani, N .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4484-4491
[4]   Cephalostatin support studies 12. The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1 [J].
Guo, CX ;
Fuchs, PL .
TETRAHEDRON LETTERS, 1998, 39 (10) :1099-1102
[5]   Cephalostatin syntheses. 10. An efficient protocol for the synthesis of unsymmetrical pyrazines. Total synthesis of dihydrocephalostatin [J].
Guo, CX ;
Bhandaru, S ;
Fuchs, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (43) :10672-10673
[6]   CEPHALOSTATIN CHEMISTRY .6. SYNTHESIS OF THE SOUTH HEXACYCLIC STEROID UNIT OF CEPHALOSTATIN-7 [J].
JEONG, JU ;
FUCHS, PL .
TETRAHEDRON LETTERS, 1995, 36 (14) :2431-2434
[7]  
JEONG JU, IN PRESS J AM CHEM S
[8]  
KIM S, IN PRESS J AM CHEM S
[9]   Interphylal product splicing:: The first total syntheses of cephalostatin 1, the north hemisphere of ritterazine G, and the highly active hybrid analogue, ritterostatin GN1N [J].
LaCour, TG ;
Guo, CX ;
Bhandaru, S ;
Boyd, MR ;
Fuchs, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :692-707
[10]  
LACOUR TG, UNPUB BIOORG MED CHE