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Synthesis of a New Family of N ‐Aryl Lactams Active on Chemesthesis and Taste
Author(s) -
Bassoli Angela,
Borgonovo Gigliola,
Busnelli Gilberto,
Morini Gabriella
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500677
Subject(s) - chemistry , menthol , benzoic acid , aryl , taste , ring (chemistry) , derivative (finance) , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , alkyl , financial economics , economics
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)