Design and synthesis of C-8 linked pyrrolobenzodiazepine-naphthalimide hybrids as anti-tumour agents

被引：61

作者：

Kamal, A ^{[1
]}

Reddy, BSN ^{[1
]}

Reddy, GSK ^{[1
]}

Ramesh, G ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2002年 / 12卷 / 15期

关键词：

D O I：

10.1016/S0960-894X(02)00326-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The facile synthesis of C-8 linked pyrrolobenzodiazepine-naphthalimide hybrid analogues is described. The compounds are prepared with varying degrees of linker length in order to probe the structural requirements for optimal in vitro anti-tumour activity. Some of these new hybrid compounds showed higher cytotoxic activity than the existing natural and synthetic pyrrolo[2,1-c][1,4]benzodiazepines. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1933 / 1935

页数：3

共 20 条

[1] Synthesis, in vitro antiproliferative activity, and DNA-binding properties of hybrid molecules containing pyrrolo[2,1-c][1,4]benzodiazepine and minor-groove-binding oligopyrrole carriers [J].

Baraldi, PG ;

Balboni, G ;

Cacciari, B ;

Guiotto, A ;

Manfredini, S ;

Romagnoli, R ;

Spalluto, G ;

Thurston, DE ;

Howard, PW ;

Bianchi, N ;

Rutigliano, C ;

Mischiati, C ;

Gambari, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (25) :5131-5141

[2] RATIONAL DESIGN OF A HIGHLY EFFICIENT IRREVERSIBLE DNA INTERSTRAND CROSS-LINKING AGENT BASED ON THE PYRROLOBENZODIAZEPINE RING-SYSTEM [J].

BOSE, DS ;

THOMPSON, AS ;

CHING, JS ;

HARTLEY, JA ;

BERARDINI, MD ;

JENKINS, TC ;

NEIDLE, S ;

HURLEY, LH ;

THURSTON, DE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) :4939-4941

[3]

Brana M. F., 2001, Current Medicinal Chemistry - Anti-Cancer Agents, V1, P237, DOI 10.2174/1568011013354624

[4] DESIGN AND SYNTHESIS OF POTENTIAL DNA CROSS-LINKING REAGENTS BASED ON THE ANTHRAMYCIN CLASS OF MINOR GROOVE BINDING-COMPOUNDS [J].

CONFALONE, PN ;

HUIE, EM ;

KO, SS ;

COLE, GM .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :482-487

[5] Design and synthesis of novel pyrrolo[2,1-c][1,4]benzodiazepine-lexitropsin conjugates [J].

Damayanthi, Y ;

Reddy, BSP ;

Lown, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :290-292

[6] DESIGN OF SEQUENCE-SPECIFIC DNA-BINDING MOLECULES [J].

DERVAN, PB .

SCIENCE, 1986, 232 (4749) :464-471

[7] Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity [J].

Gregson, SJ ;

Howard, PW ;

Hartley, JA ;

Brooks, NA ;

Adams, LJ ;

Jenkins, TC ;

Kelland, LR ;

Thurston, DE .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (05) :737-748

[8] An efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepine.: Synthesis of the antibiotic DC-81 [J].

Hu, WP ;

Wang, JJ ;

Lin, FL ;

Lin, YC ;

Lin, SR ;

Hsu, MH .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2881-2883

[9] PROPOSED STRUCTURE OF THE ANTHRAMYCIN-DNA ADDUCT [J].

HURLEY, LH ;

PETRUSEK, R .

NATURE, 1979, 282 (5738) :529-531

[10] Solid-phase synthesis of pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones [J].

Kamal, A ;

Reddy, GSK ;

Raghavan, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (03) :387-389

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