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Full Paper
Synthesis of a New Family of N-Aryl Lactams Active on Chemesthesis and Taste
Article first published online: 31 JAN 2006
DOI: 10.1002/ejoc.200500677
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Bassoli, A., Borgonovo, G., Busnelli, G. and Morini, G. (2006), Synthesis of a New Family of N-Aryl Lactams Active on Chemesthesis and Taste. European Journal of Organic Chemistry, 2006: 1656–1663. doi: 10.1002/ejoc.200500677
Publication History
- Issue published online: 14 MAR 2006
- Article first published online: 31 JAN 2006
- Manuscript Received: 5 SEP 2005
- Abstract
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Keywords:
- N-Aryl lactams;
- Cooling compounds;
- Chemesthesis;
- Taste
Graphical Abstract
Abstract
A new class of synthetic compounds with chemesthetic activity has been identified. They have been designed ex-novo by structural similarity with known cooling compounds such as menthol, icilin and cyclic ketoenamines. 19 new derivatives have been obtained easily and in high yields by Goldberg arylation or lactam ring closure on the appropriate phenol or benzoic acid derivative. The synthetic procedures are suitable for gram-scale preparation, and the products are stable and easy to purify. 17 new compounds were submitted to preliminary sensory evaluation, and 3 of them showed cooling activity and, in some cases, tingling sensation in the oral cavity. These N-aryl lactams seem to be an interesting class of compounds to be enlarged in order to derive structure-activity relationships. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)