Structure-activity delineation of quinones related to the biologically active Calothrixin B

被引：65

作者：

Bernardo, Paul H.

Chai, Christina L. L.

Le Guen, Maurice

Smith, Geoffrey D.

Waring, Paul

机构：

[1] Australian Natl Univ, Dept Chem, Canberra, ACT 0200, Australia

[2] Australian Natl Univ, Sch Biochem & Mol Biol, Canberra, ACT 0200, Australia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2007年 / 17卷 / 01期

关键词：

SAR;

D O I：

10.1016/j.bmcl.2006.09.090

中图分类号：

R914 [药物化学];

学科分类号：

100701 [药物化学];

摘要：

Quinones such as Calothrixins A and B display a range of biological properties. As part of our ongoing studies to elucidate the mechanism of action of the Calothrixins, several related quinones were synthesized and tested for biological activity. The results of the structure-activity relationship (SAR) studies are reported here. beta 2006 Elsevier Ltd. All rights reserved.

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页码：82 / 85

页数：4

相关论文

共 18 条

[1]

OXIDATION OF PHENOLS TO QUINONES BY BIS(TRIFLUOROACETOXY)IODOBENZENE [J].

BARRET, R ;

DAUDON, M .

TETRAHEDRON LETTERS, 1990, 31 (34) :4871-4872

[2]

BERLIN V, 1981, J BIOL CHEM, V256, P4747

[3]

Synthesis, electrochemistry, and bioactivity of the cyanobacterial calothrixins and related quinones [J].

Bernardo, PH ;

Chai, CLL ;

Heath, GA ;

Mahon, PJ ;

Smith, GD ;

Waring, P ;

Wilkes, BA .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (20) :4958-4963

[4]

Friedel-Crafts acylation and metalation strategies in the synthesis of calothrixins A and B [J].

Bernardo, PH ;

Chai, CLL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) :8906-8909

[5]

A simple and concise route to calothrixin B [J].

Bernardo, PH ;

Chai, CLL ;

Elix, JA .

TETRAHEDRON LETTERS, 2002, 43 (16) :2939-2940

[6]

Role of quinones in toxicology [J].

Bolton, JL ;

Trush, MA ;

Penning, TM ;

Dryhurst, G ;

Monks, TJ .

CHEMICAL RESEARCH IN TOXICOLOGY, 2000, 13 (03) :135-160

[7]

Inhibition of bacterial RNA polymerase by the cyanobacterial metabolites 12-epi-hapalindole E isonitrile and calothrixin A [J].

Doan, NT ;

Stewart, PR ;

Smith, GD .

FEMS MICROBIOLOGY LETTERS, 2001, 196 (02) :135-139

[8]

Antitumor agents. 203. Carbazole alkaloid murrayaquinone A and related synthetic carbazolequinones as cytotoxic agents [J].

Itoigawa, M ;

Kashiwada, Y ;

Ito, C ;

Furukawa, H ;

Tachibana, Y ;

Bastow, KF ;

Lee, KH .

JOURNAL OF NATURAL PRODUCTS, 2000, 63 (07) :893-897

[9]

MARTIN R, 1988, J CHEM SOC P1, P235

[10]

RAPID COLORIMETRIC ASSAY FOR CELLULAR GROWTH AND SURVIVAL - APPLICATION TO PROLIFERATION AND CYTO-TOXICITY ASSAYS [J].

MOSMANN, T .

JOURNAL OF IMMUNOLOGICAL METHODS, 1983, 65 (1-2) :55-63