Synthesis and antitumour activity of pyrene-linked pyrrolo [2,1-c][1,4]benzodiazepine hybrids

被引：54

作者：

Kamal, A ^{[1
]}

Ramesh, G ^{[1
]}

Srinivas, O ^{[1
]}

Ramulu, P ^{[1
]}

机构：

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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 02期

关键词：

pyrrolobenzodiazepines; pyrene amine; cytotoxity; DNA-binding affinity;

D O I：

10.1016/j.bmcl.2003.10.050

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Pyrene-linked pyrrolobenzodiazepine hybrids have been synthesized that exhibit potential anticancer activity in a number of human tumour cell lines. These hybrids also exhibit much enhanced DNA-binding ability in comparison to the parent pyrrolobenzodiazepine ring system (DC-81). (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：471 / 474

页数：4

共 23 条

[1] (1-PYRENYLMETHYL)AMINO ALCOHOLS, A NEW CLASS OF ANTITUMOR DNA INTERCALATORS - DISCOVERY AND INITIAL AMINE SIDE-CHAIN STRUCTURE ACTIVITY STUDIES [J].

BAIR, KW ;

TUTTLE, RL ;

KNICK, VC ;

CORY, M ;

MCKEE, DD .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2385-2393

[2] 2-[(ARYLMETHYL)AMINO]-2-METHYL-1,3-PROPANEDIOL DNA INTERCALATORS - AN EXAMINATION OF THE EFFECTS OF AROMATIC RING VARIATION ON ANTITUMOR-ACTIVITY AND DNA-BINDING [J].

BAIR, KW ;

ANDREWS, CW ;

TUTTLE, RL ;

KNICK, VC ;

CORY, M ;

MCKEE, DD .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (07) :1983-1990

[3] Polycyclic aromatic compounds as anticancer agents: Structure-activity relationships of chrysene and pyrene derivatives [J].

Banik, BK ;

Becker, FF .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (03) :593-605

[4] Polycyclic aromatic compounds as anticancer agents: Synthesis and biological evaluation of some chrysene derivatives [J].

Becker, FF ;

Banik, BK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (20) :2877-2880

[5] EFFECT OF LINKER LENGTH ON DNA-BINDING AFFINITY, CROSS-LINKING EFFICIENCY AND CYTOTOXICITY OF C8-LINKED PYRROLOBENZODIAZEPINE DIMERS [J].

BOSE, DS ;

THOMPSON, AS ;

SMELLIE, M ;

BERARDINI, MD ;

HARTLEY, JA ;

JENKINS, TC ;

NEIDLE, S ;

THURSTON, DE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (20) :1518-1520

[6] 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

[7] Synthesis and DNA-binding affinity of A-C8/C-C2 alkoxyamido-linked pyrrolo[2,1-c][1,4]benzodiazepine dimers [J].

Kamal, A ;

Ramulu, P ;

Srinivas, O ;

Ramesh, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (22) :3955-3958

[8] Synthesis of novel C2 and C2-C8 linked pyrrolo[2,1-c][1,4]benzodiazepine-naphthalimide hybrids as DNA-binding agents [J].

Kamal, A ;

Srinivas, O ;

Ramulu, P ;

Ramesh, G ;

Kumar, PP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (20) :3577-3581

[9] Synthesis of C-8 methanesulphonate substituted pyrrolobenzodiazepines as potential antitumour agents [J].

Kamal, A ;

Ramulu, P ;

Srinivas, O ;

Ramesh, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (20) :3517-3519

[10] Design and synthesis of novel chrysene-linked pyrrolo[2,1-c] [1,4]-benzodiazepine hybrids as potential DNA-binding agents [J].

Kamal, A ;

Ramesh, G ;

Ramulu, P ;

Srinivas, O ;

Rehana, T ;

Sheelu, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (20) :3451-3454

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