Organocatalyzed Novel Synthetic Methodology for Highly Functionalized Piperidines as Potent -Glucosidase Inhibitors
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- 作者：Ariba Farooq ; Lubna Shahazadi ; Marek Bajda ; Nisar Ullah ; Abdul Rauf ; Sohail Anjum Shahzad ; Ather Farooq Khan ; Muhammad Ashraf and Muhammad Yar
- 刊名：Archiv der Pharmazie
- 出版年：2016
- 出版时间：September 2016
- 年：2016
- 卷：349
- 期：9
- 页码：724-732
- 全文大小：987K
- ISSN：1521-4184
文摘
An efficient atom-economic one-pot synthesis of highly functionalized piperidines was achieved by catalytic multicomponent reaction. A wide range of heterogeneous and homogenous catalysts were explored; however, promising results were achieved when a β-keto-ester was reacted with selected aromatic aldehydes and anilines by using N-acetyl glycine (NAG) as catalyst. The implication of this methodology is straightforward since the products were precipitated out from the reaction solution, eliminating the need of column chromatography purifications. The synthesized piperidines were screened against α-glucosidase inhibition, which revealed that these compounds were very active inhibitors, and some of the compounds showed even better inhibition than the reference compound, at low micromolar concentrations. In silico molecular modeling was also performed to investigate the binding modes of the compounds into the active sites of the target protein.