Synthesis of a new family of N-aryl lactams active on chemesthesis and taste
Synthesis of a new family of N-aryl lactams active on chemesthesis and taste
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DOI：
10.1002/ejoc.200500677
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发表时间：
2006-04
影响因子：
2.8
通讯作者：
A. Bassoli;Gigliola Borgonovo;G. Busnelli;G. Morini
中科院分区：
文献类型：
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作者：
A. Bassoli;Gigliola Borgonovo;G. Busnelli;G. Morini
已经鉴定出一类具有化学活性的新型合成化合物。它们是通过与已知的清凉化合物（如薄荷醇、西林和环酮烯胺）结构相似而重新设计的。通过对适当的苯酚或苯甲酸衍生物进行 Goldberg 芳基化或内酰胺闭环，可以轻松且高产率地获得 19 种新衍生物。该合成工艺适合克级制备，产品稳定且易于纯化。 17 种新化合物已接受初步感官评价，其中 3 种表现出清凉活性，在某些情况下还表现出口腔刺痛感。这些 N-芳基内酰胺似乎是一类有趣的化合物，需要对其进行扩展，以得出结构-活性关系。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 德国, 2006)
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)