Synthesis of benzo analogs of oxoarcyriaflavins and caulersine

被引:26
作者
Bourderioux, Aurelie [1 ]
Routier, Sylvain [1 ]
Beneteau, Valerie [1 ]
Merour, Jean-Yves [1 ]
机构
[1] Univ Orleans, CNRS 6005, Inst Chim Organ Analyt, UMR, F-45067 Orleans, France
关键词
D O I
10.1016/j.tet.2007.06.118
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the course of a program aimed at designing new antitumor agents, we were interested in the synthesis of mixed structures of maleimidophenyl carbazoles and natural product caulersine as potential CDK inhibitors. This was performed through an efficient four-step sequence starting from indole or 3-formyl-N-Boc indole. 5H-Benzocycloheptaindol-6-one derivatives equipped with a fused maleimide (oxophenylarcyriaflavins) or a methyl ester ( benzo analog of caulersine) on the central tropone ring were thus obtained. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9465 / 9475
页数:11
相关论文
共 45 条
[1]   OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].
BAL, BS ;
CHILDERS, WE ;
PINNICK, HW .
TETRAHEDRON, 1981, 37 (11) :2091-2096
[2]   4H-BENZO[4,5]CYCLOHEPTA[1,2-B]THIOPHENE - UNTERSUCHUNGEN UBER SYNTHETISCHE ARZNEIMITTEL .15. [J].
BASTIAN, JM ;
EBNOTHER, A ;
JUCKER, E ;
RISSI, E ;
STOLL, AP .
HELVETICA CHIMICA ACTA, 1966, 49 :214-&
[3]   Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions [J].
Bellina, Fabio ;
Rossi, Renzo .
TETRAHEDRON, 2006, 62 (31) :7213-7256
[4]   Synthesis of indolocarbazole quinones;: potent aryl hydrocarbon receptor ligands [J].
Bergman, J ;
Wahlström, N ;
Yudina, LN ;
Tholander, J ;
Lidgren, G .
TETRAHEDRON, 2002, 58 (07) :1443-1452
[5]   Indolocarbazoles [J].
Bergman, J ;
Janosik, T ;
Wahlström, N .
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 80, 2001, 80 :1-71
[6]   Drugging cell cycle kinases in cancer therapy [J].
Blagden, S ;
de Bono, J .
CURRENT DRUG TARGETS, 2005, 6 (03) :325-335
[7]   First efficient synthesis of novel oxophenyl-arcyriaflavin analogs [J].
Bourderioux, A ;
Routier, S ;
Bénéteau, V ;
Mérour, JY .
TETRAHEDRON LETTERS, 2005, 46 (36) :6071-6074
[8]   SYNTHESIS OF ARCYRIARUBIN B AND RELATED BISINDOLYLMALEIMIDES [J].
BRENNER, M ;
REXHAUSEN, H ;
STEFFAN, B ;
STEGLICH, W .
TETRAHEDRON, 1988, 44 (10) :2887-2892
[9]   Targeting the cell division cycle in cancer: CDK and cell cycle checkpoint kinase inhibitors [J].
Collins, I ;
Garrett, MD .
CURRENT OPINION IN PHARMACOLOGY, 2005, 5 (04) :366-373
[10]   Cyclin-dependent kinase inhibitors [J].
Dai, Y ;
Grant, S .
CURRENT OPINION IN PHARMACOLOGY, 2003, 3 (04) :362-370