SYNTHESIS OF C-NOR-4,6-SECOCAMPTOTHECIN AND RELATED-COMPOUNDS

被引：5

作者：

KURIHARA, T

TANNO, H

TAKEMURA, S

HARUSAWA, S

YONEDA, R

机构：

[1] Osaka University of Pharmaceutical Sciences, Osaka, 580

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1993年 / 30卷 / 03期

关键词：

D O I：

10.1002/jhet.5570300311

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-nor-4,6-Secocamptothecin 2, 4-ethyl-4-hydroxy-6-(2-quinolinyl)-1H-pyrano[3,4-c]pyridine-3,8(4H,7H)-dione, lacking the C-ring of camptothecin 1, and its related compounds 3 and 4 were prepared from ethyl quinoline-2-carboxylate 7. By an analogous reaction sequences, synthesis of 6-(2-pyridinyl)-1H-pyrano[3,4-c]-pyridine-3,8(4H,7H)-dione derivatives 5 and 6, which contain the B, D, and E ring of 1, were achieved.

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页码：643 / 652

页数：10

相关论文

共 16 条

[1] REACTIONS WITH INDOLE-DERIVATIVES .17. BIOGENETICALLY ORIENTATED TOTAL-SYNTHESIS OF DL-CAMPTOTHECIN AND 7-CHLOROCAMPTOTHECIN [J].

BOCH, M ;

WINTERFELDT, E ;

NELKE, JM ;

RADUNZ, H ;

PIKE, D ;

KORTH, T .

CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (07) :2126-+

[2]

Cai J-C., 1983, ALKALOIDS CHEM PHARM, VVol. 21, P101

[3] SYNTHESIS AND BIOLOGICAL EVALUATION OF DE-AB-CAMPTOTHECIN [J].

DANISHEF.S ;

ETHEREDG.SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (23) :3430-3432

[4]

GRAS JL, 1990, ORG SYNTH, V7, P332

[5]

HELBLING AM, 1976, HELV CHIM ACTA, V59, P938

[6] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES [J].

HOFFMANN, HMR ;

RABE, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :94-110

[7]

KANO S, 1979, CHEM PHARM BULL, V27, P2450

[8] SYNTHESIS OF WATER-SOLUBLE (AMINOALKYL)CAMPTOTHECIN ANALOGS - INHIBITION OF TOPOISOMERASE-I AND ANTITUMOR-ACTIVITY [J].

KINGSBURY, WD ;

BOEHM, JC ;

JAKAS, DR ;

HOLDEN, KG ;

HECHT, SM ;

GALLAGHER, G ;

CARANFA, MJ ;

MCCABE, FL ;

FAUCETTE, LF ;

JOHNSON, RK ;

HERTZBERG, RP .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) :98-107

[9] REACTIONS WITH INDOLE-DERIVATIVES .28. ALKYLATION OF CAMPTOTHECIN-INTERMEDIATES - NEW APPROACH TO CAMPTOTHECIN [J].

KROHN, K ;

WINTERFELDT, E .

CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (09) :3030-3042

[10] BIOACTIVATION AS A MODEL FOR DRUG DESIGN BIOREDUCTIVE ALKYLATION [J].

MOORE, HW .

SCIENCE, 1977, 197 (4303) :527-532