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Full Paper
Synthesis of Novel Macrolactam and Macroketone Analogues of Migrastatin from D-Glucal and Comparison with Macrolactone and Acyclic Analogues: A Dorrigocin A Congener Is a Potent Inhibitor of Gastric Cancer Cell Migration
Article first published online: 18 FEB 2008
DOI: 10.1002/ejoc.200701192
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Anquetin, G., Horgan, G., Rawe, S., Murray, D., Madden, A., MacMathuna, P., Doran, P. and Murphy, P. V. (2008), Synthesis of Novel Macrolactam and Macroketone Analogues of Migrastatin from D-Glucal and Comparison with Macrolactone and Acyclic Analogues: A Dorrigocin A Congener Is a Potent Inhibitor of Gastric Cancer Cell Migration. Eur. J. Org. Chem., 2008: 1953–1958. doi: 10.1002/ejoc.200701192
Publication History
- Issue published online: 19 MAR 2008
- Article first published online: 18 FEB 2008
- Manuscript Received: 17 DEC 2007
Funded by
- Science Foundation Ireland. Grant Number: 03/IBN/B352
- Abstract
- Article
- References
- Cited By
Keywords:
- Carbohydrates;
- Tumour cell migration inhibitor;
- Cancer;
- Horner olefination;
- Migrastatin;
- Dorrigocin A;
- Natural products
Abstract
Novel macrolactam and macroketone analogues of the migrastatin macrolide core have been synthesised from tri-O-acetyl-D-glucal in order to facilitate structure-activity studies. The Horner olefination, followed by ring-closing metathesis were key steps in the synthesis of the macroketone. The ability of the macroketone and macrolactam derivatives to inhibit the migration of gastric tumour cells as determined using a transwell migration assay were compared with macrolactone analogues and dorrigocin A analogues. One dorrigocin A congener was the most potent inhibitor of gastric cancer cell migration.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)