Photochemistry of tosylstilbenoids in the preparation of complex heterocyclic compounds. Synthesis of a cyclopropafuroindolone analogue of the DNA-alkylating section of the antitumor compound CC-1065

被引：10

作者：

Enjo, J

Castedo, L

Tojo, G ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela 15706, Spain

[2] Univ Santiago de Compostela, Unidad Asociada, CSIC, Santiago De Compostela 15706, Spain

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 09期

关键词：

D O I：

10.1021/ol015717l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel photocyclization of tosylstilbenoids is used in the preparation of a cyclopropafuroindolone analogue of the DNA-alkylating unit of the antitumor compound CC-1065.

引用

页码：1343 / 1345

页数：3

共 18 条

[1] Photochemical ring closure of 1-tosyl-1,2-diarylethenes [J].

Antelo, B ;

Castedo, L ;

Delamano, J ;

Gomez, A ;

Lopez, C ;

Tojo, G .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) :1188-1189

[2] Synthesis and cytotoxicity of 5-amino-1-(chloromethyl)-3-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indole (amino-seco-CBI-TMI) and related 5-alkylamino analogues:: New DNA minor groove alkylating agents [J].

Atwell, GJ ;

Tercel, M ;

Boyd, M ;

Wilson, WR ;

Denny, WA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9414-9420

[3] CC-1065 and the duocarmycins: Synthetic studies [J].

Boger, DL ;

Boyce, CW ;

Garbaccio, RM ;

Goldberg, JA .

CHEMICAL REVIEWS, 1997, 97 (03) :787-828

[4] SYNTHESIS AND PRELIMINARY EVALUATION OF AGENTS INCORPORATING THE PHARMACOPHORE OF THE DUOCARMYCIN PYRINDAMYCIN ALKYLATION SUBUNIT - IDENTIFICATION OF THE CC-1065 DUOCARMYCIN COMMON PHARMACOPHORE [J].

BOGER, DL ;

ISHIZAKI, T ;

ZARRINMAYEH, H ;

KITOS, PA ;

SUNTORNWAT, O .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4499-4502

[5] Selective metal cation activation of a DNA alkylating agent:: Synthesis and evaluation of methyl 1,2,9,9a-tetrahydrocyclopropa[c]pyrido[3,2-e]indol-4-one-7-carboxylate (CPyI) [J].

Boger, DL ;

Boyce, CW .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13) :4088-4100

[6] Synthesis and evaluation of 1,2,8,8a-tetrahydrocyclopropa[c]pyrrolo[3,2-e]indol-4(5H)-one, the parent alkylation subunit of CC-1065 and the duocarmycins:: Impact of the alkylation subunit substituents and its implications for DNA alkylation catalysis [J].

Boger, DL ;

Santillan, A ;

Searcey, M ;

Brunette, SR ;

Wolkenberg, SE ;

Hedrick, MP ;

Jin, Q .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13) :4101-4111

[7] CC-1065 and the duocarmycins: Understanding their biological function through mechanistic studies [J].

Boger, DL ;

Johnson, DS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (13-14) :1438-1474

[8]

CASTEDO L, 1994, HETEROCYCLES, V38, P495

[9]

CASTEDO L, IN PRESS J AM CHEM S

[10] THE STRUCTURE OF CC-1065, A POTENT ANTI-TUMOR AGENT, AND ITS BINDING TO DNA [J].

CHIDESTER, CG ;

KRUEGER, WC ;

MIZSAK, SA ;

DUCHAMP, DJ ;

MARTIN, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (25) :7629-7635

← 1 2 →