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Synthesis 2005(9): 1543-1549  
DOI: 10.1055/s-2005-865356
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Biological Evaluation of Some Furanones as Putative Chitinase Inhibitors

Gilles Grossmanna, Benoît Joliveta, Marc Bornanda, Urs Séquin*a, Klaus-Dieter Spindler*b
a Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland
Fax: +41(61)2671103; e-Mail: urs.sequin@unibas.ch;
b Department of General Zoology and Endocrinology, University of Ulm, 89069 Ulm, Germany
Further Information

Publication History

Received 11 February 2005
Publication Date:
02 May 2005 (online)

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Abstract

Analogs of naturally occurring furanones that were reported to be weak inhibitors of Serratia marcescens chitinases were prepared and tested towards various chitinases. Some of these compounds - but not the natural products - were found to be weak but selective inhibitors; all glycosylated analogs tested were inactive. Activation of the plant enzyme hevamine was observed in one case, which is unusual.

Key words

chitinases - enzyme inhibitors - furan-2(5H)-ones - gly­cosylation - hevamine activation

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Performed by M. Neuburger, Departement Chemie, Universität Basel. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication. CCDC-number for 12b: 261974. Copies of the data can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44 1223 336033 or E-mail: deposit@ccdc.cam.ac.uk].