Hemisynthesis of rhazinilam analogues: Structure-activity relationships on tubulin-microtubule system

被引:53
作者
David, B
Sevenet, T
Thoison, O
Awang, K
Pais, M
Wright, M
Guenard, D
机构
[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
[2] CNRS,PHARMACOL & TOXICOL FONDAMENTALES LAB,TOULOUSE,FRANCE
关键词
D O I
10.1016/S0960-894X(97)00391-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Semi-synthesis of derivatives of rhazinilam, an antitubulin compound, delineated some molecular features necessary for biological activity. In the course of this study, the formation of rhazinilam from 1,2-didehydroaspidospermidine is reexamined and a new mechanism is proposed. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:2155 / 2158
页数:4
相关论文
共 14 条
[1]   OCCURRENCE OF GEISSOSCHIZINE AND OTHER MINOR BIOGENETICALLY RELATED ALKALOIDS IN RHAZYA-STRICTA [J].
BANERJI, A ;
MAJUMDER, PL ;
CHATTERJEE, A .
PHYTOCHEMISTRY, 1970, 9 (07) :1491-+
[2]   RHAZINILAM MIMICS THE CELLULAR EFFECTS OF TAXOL BY DIFFERENT MECHANISMS OF ACTION [J].
DAVID, B ;
SEVENET, T ;
MORGAT, M ;
GUENARD, D ;
MOISAND, A ;
TOLLON, Y ;
THOISON, O ;
WRIGHT, M .
CELL MOTILITY AND THE CYTOSKELETON, 1994, 28 (04) :317-326
[3]  
DAVID B, 1990, THESIS PARIS FRANCE
[4]  
DESILVA KT, 1972, TETRAHEDRON LETT, V10, P913
[5]  
GOH SH, 1982, TETRAHEDRON LETT, V27, P2501
[6]  
GUENARD D, UNPUB
[7]   FACILE INTRODUCTION OF ESTER GROUPS INTO PYRROLE NUCLEUS VIA TRICHLOROACETYLATION AND ALCOHOLYSIS [J].
HARBUCK, JW ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (23) :3618-&
[8]   RELATIONSHIPS BETWEEN THE STRUCTURES OF TAXOL AND BACCATINE-III DERIVATIVES AND THEIR INVITRO ACTION ON THE DISASSEMBLY OF MAMMALIAN BRAIN AND PHYSARUM AMEBAL MICROTUBULES [J].
LATASTE, H ;
SENILH, V ;
WRIGHT, M ;
GUENARD, D ;
POTIER, P .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1984, 81 (13) :4090-4094
[9]  
LEWIN G, 1980, HETEROCYCLES, V14, P1915
[10]   MICROBIAL HYDROXYLATIONS OF BETA-CARBOLINE DERIVATIVES [J].
NEEF, G ;
EDER, U ;
PETZOLDT, K ;
SEEGER, A ;
WIEGLEPP, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (06) :366-367