Issue 9, 2010
From the journal:

Organic & Biomolecular Chemistry

Synthesis of antitumour (1H-1,2,3-triazol-4-yl)-4-hydroxycyclohexa-2,5-dien-1-ones by copper-catalysed Huisgen cycloadditions†

Andrew J. McCarroll,a   Charles S. Matthews,b   Geoffrey Wells,‡a   Tracey D. Bradshawb  and  Malcolm F. G. Stevens*ab  

* Corresponding authors

a Pharminox Ltd, Biocity, Pennyfoot Street, Nottingham

b Centre for Biomolecular Sciences, School of Pharmacy, University of Nottingham, Nottingham, U.K.
E-mail: malcolm.stevens@nottingham.ac.uk
Fax: +44 115 951 3412
Tel: +44 115 951 3414

Abstract

4-Ethynyl-4-hydroxycyclohexa-2,5-dien-1-one 5 undergoes cycloaddition reactions with a range of substituted azides in the presence of copper salts to form 1,4-disubstituted triazoles 8–11 bearing the 4-hydroxycyclohexa-2,5-dien-1-one (quinol) pharmacophore; one example of an isomeric 1,5-disubstituted triazole 12 was formed from 5 and benzyl azide in the presence of a ruthenium catalyst. Compounds were screened for growth-inhibitory activity against five cancer cell lines of colon, breast and lung origin, but were overall less potent than the benzothiazolyl- and indolyl-substituted quinols 2 and 3.

Graphical abstract: Synthesis of antitumour (1H-1,2,3-triazol-4-yl)-4-hydroxycyclohexa-2,5-dien-1-ones by copper-catalysed Huisgen cycloadditions

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Article information

DOI
https://doi.org/10.1039/B920039H
Article type
Paper
Submitted
25 Sep 2009
Accepted
08 Feb 2010
First published
03 Mar 2010

Org. Biomol. Chem., 2010,8, 2078-2084

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Synthesis of antitumour (1H-1,2,3-triazol-4-yl)-4-hydroxycyclohexa-2,5-dien-1-ones by copper-catalysed Huisgen cycloadditions

A. J. McCarroll, C. S. Matthews, G. Wells, T. D. Bradshaw and M. F. G. Stevens, Org. Biomol. Chem., 2010, 8, 2078 DOI: 10.1039/B920039H

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