Synthesis of isogranulatimide analogues possessing a pyrrole moiety instead of an imidazole heterocycle

被引：32

作者：

Hugon, B

Pfeiffer, B

Renard, P

Prudhomme, M ^{[1
]}

机构：

[1] Univ Clermont Ferrand, Synth & Etude Syst Interet Biol, CNRS, UMR 6504, F-63177 Aubiere, France

[2] Labs SERVIER, F-92415 Courbevoie, France

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 20期

关键词：

G2 checkpoint inhibitors; isogranulatimide; pyrrolo[3,4-c]carbazole;

D O I：

10.1016/S0040-4039(03)00837-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient four step synthesis from commercial indoles of isogranulatimide analogues is reported. In the new compounds, the imidazole moiety is replaced by a pyrrole unit, the indole part is substituted or not in 5-position and the nitrogen of the imide moiety bears or not a methyl substituent. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：3927 / 3930

页数：4

相关论文

共 16 条

[1] ON THE [4+2] CYCLOADDITION APPROACH TO INDOLO[2,3-A]CARBAZOLES [J].

BARRY, JF ;

WALLACE, TW ;

WALSHE, NDA .

TETRAHEDRON, 1995, 51 (47) :12797-12806

[2] Reactions of 1,2-bis(1H-indol-2-yl)ethane:: Formation of indolo[2,3-c]carbazole and cyclohept[1,2-b:5,4-b′]bisindole derivatives [J].

Bergman, J ;

Janosik, T ;

Yudina, L ;

Desarbre, E ;

Lidgren, G ;

Venemalm, L .

TETRAHEDRON, 2000, 56 (13) :1911-1916

[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]

BOCCHI V, 1982, SYNTHESIS-STUTTGART, P1096

[5] SYNTHESIS AND SPECTROSCOPIC CHARACTERISTICS OF 2,3'-BIINDOLYLS AND 2,2'-INDOLYLPYRROLES [J].

BOCCHI, V ;

PALLA, G .

TETRAHEDRON, 1984, 40 (17) :3251-3256

[6] Molecular orbital calculations, experimental and theoretical UV spectra of granulatimides and didemnimides, biologically active polycyclic heteroaromatic alkaloids from the ascidian Didemnum granulatum [J].

Camargo, AJ ;

Oliveira, JHHL ;

Trsic, M ;

Berlinck, RGS .

JOURNAL OF MOLECULAR STRUCTURE, 2001, 559 (1-3) :67-77

[7]

CHENE P, 2000, CURR MED CHEM ANTICA, V1, P151

[8] Blocking CHK1 expression induces apoptosis and abrogates the G2 checkpoint mechanism [J].

Luo, Y ;

Rockow-Magnone, SK ;

Kroeger, PE ;

Frost, L ;

Chen, ZH ;

Han, EKH ;

Ng, SC ;

Simmer, RL ;

Giranda, VL .

NEOPLASIA, 2001, 3 (05) :411-419

[9] Cell cycle checkpoints and their inactivation in human cancer [J].

Molinari, M .

CELL PROLIFERATION, 2000, 33 (05) :261-274

[10] Improved synthesis of isogranulatimide, a G2 checkpoint inhibitor. Syntheses of didemnimide C, isodidemnimide A, neodidemnimide A, 17-methylgranulatimide, and isogranulatimides A-C [J].

Piers, E ;

Britton, R ;

Andersen, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (02) :530-535