NEW APPROACHES TO PYRROLO[2,1-C][1,4]BENZODIAZEPINES - SYNTHESIS, DNA-BINDING AND CYTOTOXICITY OF DC-81

被引：0

作者：

BOSE, DS ^{[1
]}

JONES, GB ^{[1
]}

THURSTON, DE ^{[1
]}

机构：

[1] PORTSMOUTH POLYTECH,SCH PHARM & BIOMED SCI,DIV MED CHEM,PK BLDG,KING HENRY 1ST ST,PORTSMOUTH PO1 2DZ,HANTS,ENGLAND

来源：

TETRAHEDRON | 1992年 / 48卷 / 04期

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D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two routes to the naturally occurring DNA-binding antitumour antibiotic DC-81 are described, one of which involves a novel cyclization process based on acid resin. The second route involves the synthesis of a new compound, 6-nitrovanillic acid, a key A-ring component of many naturally occurring PBDs. These routes have provided a sufficient quantity of DC-81 to allow complete characterization and evaluation in DNA-binding and in vitro cytotoxicity studies.

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页码：751 / 758

页数：8

相关论文

共 17 条

[1]

BOSE DS, 1990, TETRAHEDRON LETT, V31, P6903

[2] RAPID REMOVAL OF PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH 1,4-CYCLOHEXADIENE [J].

FELIX, AM ;

HEIMER, EP ;

LAMBROS, TJ ;

TZOUGRAKI, C ;

MEIENHOFER, J .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4194-4196

[3] HARD ACID AND SOFT NUCLEOPHILE SYSTEM - NEW EFFICIENT METHOD FOR REMOVAL OF BENZYL PROTECTING GROUP [J].

FUJI, K ;

ICHIKAWA, K ;

NODE, M ;

FUJITA, E .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1661-1664

[4] COVALENT BINDING OF ANTITUMOR ANTIBIOTICS IN THE MINOR GROOVE OF DNA - MECHANISM OF ACTION OF CC-1065 AND THE PYRROLO(1,4)BENZODIAZEPINES [J].

HURLEY, LH ;

NEEDHAMVANDEVANTER, DR .

ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (08) :230-237

[5] PYRROLO[1,4]BENZODIAZEPINE ANTITUMOR ANTIBIOTICS - RELATIONSHIP OF DNA ALKYLATION AND SEQUENCE SPECIFICITY TO THE BIOLOGICAL-ACTIVITY OF NATURAL AND SYNTHETIC COMPOUNDS [J].

HURLEY, LH ;

RECK, T ;

THURSTON, DE ;

LANGLEY, DR ;

HOLDEN, KG ;

HERTZBERG, RP ;

HOOVER, JRE ;

GALLAGHER, G ;

FAUCETTE, LF ;

MONG, SM ;

JOHNSON, RK .

CHEMICAL RESEARCH IN TOXICOLOGY, 1988, 1 (05) :258-268

[6]

HURLEY LH, 1984, PHARM RES-DORDR, V2, P52

[7]

JONES GB, 1991, THESIS PORTSMOUTH PO

[8] A VERSATILE AND EFFICIENT SYNTHESIS OF CARBINOLAMINE-CONTAINING PYRROLO[1,4]BENZODIAZEPINES VIA THE CYCLIZATION OF N-(2-AMINOBENZOYL)PYRROLIDINE-2-CARBOXALDEHYDE DIETHYL THIOACETALS - TOTAL SYNTHESIS OF PROTHRACARCIN [J].

LANGLEY, DR ;

THURSTON, DE .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) :91-97

[9]

MORITA T, 1978, J CHEM SOC CHEM COMM, P875

[10] EVALUATION OF THE ELECTROPHILICITY OF DNA-BINDING PYRROLO[2,1-C][1,4]BENZODIAZEPINES BY HPLC [J].

MORRIS, SJ ;

THURSTON, DE ;

NEVELL, TG .

JOURNAL OF ANTIBIOTICS, 1990, 43 (10) :1286-1292