Synthesis of granulatimide analogues bearing a maleimide instead of an imidazole heterocycle

被引:27
作者
Hugon, B
Pfeiffer, B
Renard, P
Prudhomme, M [1 ]
机构
[1] Univ Clermont Ferrand, UMR 6504, CNRS, F-63177 Aubiere, France
[2] Labs SERVIER, F-92415 Courbevoie, France
关键词
G2 checkpoint inhibitors; granulatimide; dipyrrolocarbazole tetraone;
D O I
10.1016/S0040-4039(03)00823-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis in a few steps of a new family of granulatimide analogues was performed. In the new compounds, the aromatic framework of granulatimide is modified by replacement of the imidazole unit by a maleimide moiety. The synthesis of a water-soluble analogue is also presented. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3935 / 3937
页数:3
相关论文
共 13 条
[1]   Synthesis of indolo[3,2-a]pyrrolo[3,4-c]carbazole in one step from indole and maleimide [J].
Bergman, J ;
Desarbre, E ;
Koch, E .
TETRAHEDRON, 1999, 55 (08) :2363-2370
[2]   Acid-induced dimerization of 3-(1H-indol-3-yl)maleimides.: Formation of cyclopentindole derivatives [J].
Bergman, J ;
Janosik, T ;
Koch, E ;
Pelcman, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16) :2615-2621
[3]   Granulatimide and isogranulatimide, aromatic alkaloids with G2 checkpoint inhibition activity isolated from the Brazilian ascidian Didemnum granulatum:: Structure elucidation and synthesis [J].
Berlinck, RGS ;
Britton, R ;
Piers, E ;
Lim, L ;
Roberge, M ;
da Rocha, RM ;
Andersen, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9850-9856
[4]  
Busby EC, 2000, CANCER RES, V60, P2108
[5]   Inhibition of the G2 DNA damage checkpoint and of protein kinases Chk1 and Chk2 by the marine sponge alkaloid debromohymenialdisine [J].
Curman, D ;
Cinel, B ;
Williams, DE ;
Rundle, N ;
Block, WD ;
Goodarzi, AA ;
Hutchins, JR ;
Clarke, PR ;
Zhou, BB ;
Lees-Miller, SP ;
Andersen, RJ ;
Roberge, M .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (21) :17914-17919
[6]  
Jiang XX, 2000, INT J ONCOL, V16, P971
[7]   Cyclins and cell cycle checkpoints [J].
Johnson, DG ;
Walker, CL .
ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1999, 39 :295-312
[8]   WATER-SOLUBLE DERIVATIVES OF REBECCAMYCIN [J].
KANEKO, T ;
WONG, H ;
UTZIG, J ;
SCHURIG, J ;
DOYLE, TW .
JOURNAL OF ANTIBIOTICS, 1990, 43 (01) :125-127
[9]  
Kaufmann WK, 1998, P SOC EXP BIOL MED, V217, P327
[10]  
Prudhomme Michelle, 2001, Proceedings of the American Association for Cancer Research Annual Meeting, V42, P257