New N-(phenoxydecyl)phthalimide derivatives displaying potent inhibition activity towards α-glucosidase
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- 作者：Rossana Pascale ; Alessia Carocci ; Alessia Catalano ; Giovanni Lentini ; Anna Spagnoletta ; Maria Maddalena Cavalluzzi ; Francesco De Santis ; Annalisa De Palma ; Vito Scalera ; Carlo Franchini
- 关键词：α ; -Glucosidase ; Enzyme inhibitors ; Phthalimide ; Structure– ; activity relationships ; Substituent effects
- 刊名：Bioorganic and Medicinal Chemistry
- 出版年：2010
- 出版时间：15 August 2010
- 年：2010
- 卷：18
- 期：16
- 页码：5903-5914
- 全文大小：550 K
文摘
Several members of a new family of non-sugar-type α-glucosidase inhibitors, bearing a phthalimide moiety connected to a variously substituted phenoxy ring by an alkyl chain, were synthesized and their activities were investigated. The efficacy of the inhibition activity appeared to be governed by the chain length of the substrate. Substrates possessing 10 carbons afforded the highest levels of activity, which were one to two orders of magnitude more potent than the known inhibitor 1-deoxynojirimycin (dNM). Furthermore, structure–activity relationship studies indicated a critical role of electron-withdrawing substituents at the phenoxy group for the activity. Derivatives bearing a chlorine atom along with a strong electron-withdrawing group, such as a nitro group, were the most potent of the series.