Synthesis of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones bearing a sugar moiety

被引：15

作者：

Hénon, H

Anizon, F

Pfeiffer, B

Prudhomme, M ^{[1
]}

机构：

[1] Univ Clermont Ferrand, Lab SEESIB, UMR 6504, CNRS, F-63177 Clermont Ferrand, France

[2] Inst Rech Servier, Div Rech Cancerol, F-78290 Croissy Sur Seine, France

来源：

TETRAHEDRON | 2006年 / 62卷 / 06期

关键词：

granulatimide; antitumor agents; dipyrrolo[3,4-a : 3,4-c]-carbazole-1,3,4,6-tetraone;

D O I：

10.1016/j.tet.2005.10.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a series of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones, structurally related to the G2 checkpoint inhibitor granulatimide and bearing a sugar moiety, is described. Substitutions were carried out at the 6-position of the glycosyl unit to lead to an amino substituent as observed in many biologically active compounds such as anthracyclins or staurosporines. (c) 2005 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1116 / 1123

页数：8

相关论文

共 37 条

[1] Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group [J].

Anizon, F ;

Belin, L ;

Moreau, P ;

Sancelme, M ;

Voldoire, A ;

Prudhomme, M ;

Ollier, M ;

Severe, D ;

Riou, JF ;

Bailly, C ;

Fabbro, D ;

Meyer, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (21) :3456-3465

[2] 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

[3] SYNTHESIS OF ARCYRIARUBIN B AND RELATED BISINDOLYLMALEIMIDES [J].

BRENNER, M ;

REXHAUSEN, H ;

STEFFAN, B ;

STEGLICH, W .

TETRAHEDRON, 1988, 44 (10) :2887-2892

[4] PRODUCTION AND BIOLOGICAL-ACTIVITY OF REBECCAMYCIN, A NOVEL ANTITUMOR AGENT [J].

BUSH, JA ;

LONG, BH ;

CATINO, JJ ;

BRADNER, WT .

JOURNAL OF ANTIBIOTICS, 1987, 40 (05) :668-678

[5] SEQUENCE-SELECTIVE TOPOISOMERASE-II INHIBITION BY ANTHRACYCLINE DERIVATIVES IN SV40 DNA - RELATIONSHIP WITH DNA-BINDING AFFINITY AND CYTOTOXICITY [J].

CAPRANICO, G ;

ZUNINO, F ;

KOHN, KW ;

POMMIER, Y .

BIOCHEMISTRY, 1990, 29 (02) :562-569

[6]

Chaires JB, 1997, BIOPOLYMERS, V44, P201, DOI 10.1002/(SICI)1097-0282(1997)44:3<201::AID-BIP2>3.0.CO

[7]

2-Z

[8]

Chen L. W. L, 2003, WO Patent, Patent No. 03051900

[9] Synthesis of rebeccamycin and 11-dechlororebeccamycin [J].

Faul, MM ;

Winneroski, LL ;

Krumrich, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2465-2470

[10] Synthesis and biological studies of novel neurotensin(8-13) mimetics [J].

Feng, HJ ;

Zaidi, J ;

Cusack, B ;

Richelson, E .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (12) :3849-3858

← 1 2 3 4 →