Synthesis and spectroscopic characterisation of a combinatorial library based on the fungal natural product 3-chloro-4-hydroxyphenylacetamide

被引：20

作者：

Davis, Rohan A. ^{[1
]}

Pierens, Gregory K.

Parsons, Peter G.

机构：

[1] Griffith Univ, Eskitis Inst Cell & Mol Therapies, Nat Prod Discovery, Brisbane, Qld 4111, Australia

[2] Queensland Inst Med Res, Melanoma Genom Grp, Brisbane, Qld 4006, Australia

来源：

MAGNETIC RESONANCE IN CHEMISTRY | 2007年 / 45卷 / 05期

关键词：

H-1; NMR; C-13; combinatorial synthesis; natural product template; cytotoxicity; MM96L; DU145;

D O I：

10.1002/mrc.1984

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Parallel solution-phase chemistry has yielded a series of secondary amide analogues of the fungal natural product 3-chloro-4-hydroxyphenylacetamide. 3-Chloro4-hydroxyphenylacetic acid was coupled to a variety of primary amines using 1-ethyl-3-(3'-dimethylaminopropyl)-carbodiimide hydrochloride. The desired products were obtained in good yield and high purity following rapid silica purification. All analogues were spectroscopically characterised using NMR, UV, IR and MS data. One compound displayed moderate cytotoxicity against the human melanoma and prostate cell lines, MM96L and DU145. Copyright (c) 2007 John Wiley & Sons, Ltd.

引用

页码：442 / 445

页数：4

共 19 条

[1] The role of natural product chemistry in drug discovery [J].

Butler, MS .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (12) :2141-2153

[2] Traceless solid-phase synthesis of carbolinones [J].

Chern, MS ;

Shih, YK ;

Dewang, PM ;

Li, WR .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (06) :855-858

[3] The isolation and synthesis of 3-chloro-4-hydroxy-phenylacetamide produced by a plant-associated microfungus of the genus Xylaria [J].

Davis, RA ;

Watters, D ;

Healy, PC .

TETRAHEDRON LETTERS, 2005, 46 (06) :919-921

[4] The synthesis of a combinatorial library using a tambjamine natural product template [J].

Davis, RA ;

Carroll, AR ;

Quinn, RJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2001, 54 (06) :355-359

[5] Solution phase synthesis of libraries of polycyclic natural product analogue by cascade radical annulation: Synthesis of a 64-member library of mappicine analogues and a 48-member library of mappicine ketone analogues [J].

de Frutos, O ;

Curran, DP .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (06) :639-649

[6] Solution- and solid-phase strategies for the design, synthesis, and screening of libraries based on natural product templates: A comprehensive survey [J].

Hall, DG ;

Manku, S ;

Wang, F .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2001, 3 (02) :125-150

[7] Natural products as scaffolds for chemical diversification: Solution-phase parallel synthesis of a series of naringin analogues [J].

Hanessian, S ;

Kothakonda, KK .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (06) :837-842

[8]

Henkel T, 1999, ANGEW CHEM INT EDIT, V38, P643, DOI 10.1002/(SICI)1521-3773(19990301)38:5<643::AID-ANIE643>3.0.CO

[9]

2-G

[10] Scaffold architecture and pharmacophoric properties of natural products and trade drugs: Application in the design of natural product-based combinatorial libraries [J].

Lee, ML ;

Schneider, G .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2001, 3 (03) :284-289

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