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Synthesis of New 2,5-Dihydro-Pyrroles Through Ugi Reaction and Their Evaluations As Novel Α-Glucosidase Inhibitors Publisher



F Khan Mohammadi FATEMEH ; R Yazzaf ROZITA ; S Mojtabavi SOMAYEH ; Ma Faramarzi Mohammad ALI ; M Mahdavic MOHAMMAD
Authors

Source: ChemistrySelect Published:2025


Abstract

A metal-free post-transformation of the Ugi four-component reaction is disclosed for the efficient construction of 2,5-dihydropyrroles, which are important heterocyclic compounds. The synthetic process involves the Ugi-4CR using readily available starting materials such as N-phenylglycine derivatives, propargylamine, and various aldehydes and isocyanides, followed by consecutive annulation under basic conditions. A new C─C bond is formed through a 5-endo-dig cyclization during this construction. The efficiency of this methodology is demonstrated by the rapid synthesis of ten 3-pyrroline derivatives, exhibiting significant building-block diversity and structural complexity, all accomplished within two operational steps. Furthermore, all synthesized compounds 6a-j were evaluated against α-glucosidase as an important target in the treatment of diabetes. Obtained in vitro data demonstrated that all compounds 6a-j were more potent than standard inhibitor and the most potent compound among them was compound 6b with inhibitory activity around 3.5-folds more than standard inhibitor. © 2025 Elsevier B.V., All rights reserved.
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