Synthesis of isogranulatimides A and B analogues possessing a 7-azaindole unit instead of an indole moiety

被引：25

作者：

Hugon, B

Pfeiffer, B

Renard, P

Prudhomme, M ^{[1
]}

机构：

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

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

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 24期

关键词：

G2 checkpoint inhibitors; isogranulatimide; rebeccamycin;

D O I：

10.1016/S0040-4039(03)00924-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a new family of isogranulatimides analogues is described in which a 7-azaindole replaces the indole moiety. The key step is the photocyclization of the aza didemnimide intermediates which leads to two isomeric analogues of isogranulatimides A and B. A derivative bearing a carbohydrate part linked to the azaindole via a beta-N-glycosidic bond was also prepared. (C) 2003 Elsevier Science Ltd. All rights reserved.

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收藏

页码：4607 / 4611

页数：5

相关论文

共 21 条

[11] Synthesis and reactivity of 7-azaindoles (1H-pyrrolo[2,3-b]pyridine) [J].

Mérour, JY ;

Joseph, B .

CURRENT ORGANIC CHEMISTRY, 2001, 5 (05) :471-506

[12] Synthesis of dissymmetric indolocarbazole glycosides using the Mitsunobu reaction at the glycosylation step [J].

Ohkubo, M ;

Nishimura, T ;

Jona, H ;

Honma, T ;

Ito, S ;

Morishima, H .

TETRAHEDRON, 1997, 53 (17) :5937-5950

[13] 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

[14]

Prudhomme M, 1997, CURR PHARM DESIGN, V3, P265

[15]

Roberge M, 1998, CANCER RES, V58, P5701

[16] First synthesis of symmetrical and non-symmetrical aza indolocarbazoles derivatives [J].

Routier, S ;

Coudert, G ;

Mérour, JY ;

Caignard, DH .

TETRAHEDRON LETTERS, 2002, 43 (14) :2561-2564

[17]

SUGUMA M, 1999, CANCER RES, V59, P5887

[18] Synthesis and cyclisation of didemnimide C and its imidazol-1-yl isomer [J].

Terpin, A ;

Winklhofer, C ;

Schumann, S ;

Steglich, W .

TETRAHEDRON, 1998, 54 (09) :1745-1752

[19] UCN-01, a potent abrogator of G(2) checkpoint function in cancer cells with disrupted p53 [J].

Wang, QZ ;

Fan, SJ ;

Eastman, A ;

Worland, PJ ;

Sausville, EA ;

OConnor, PM .

JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1996, 88 (14) :956-965

[20] New synthetic route to granulatimide and its structural analogues [J].

Yoshida, T ;

Nishiyachi, M ;

Nakashima, N ;

Murase, M ;

Kotani, E .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (06) :872-876