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An Efficient and Targeted Synthetic Approach Towards New Highly Substituted 6-Amino-Pyrazolo[1,5-A]Pyrimidines With Α-Glucosidase Inhibitory Activity Publisher Pubmed



Peytam F1, 2 ; Adib M1 ; Shourgeshty R1, 2 ; Firoozpour L2 ; Rahmanianjazi M2 ; Jahani M1 ; Moghimi S2 ; Divsalar K3 ; Faramarzi MA4 ; Mojtabavi S4 ; Safari F5 ; Mahdavi M6 ; Foroumadi A2, 3
Authors

Source: Scientific Reports Published:2020


Abstract

In an attempt to find novel α-glucosidase inhibitors, an efficient, straightforward reaction to synthesize a library of fully substituted 6-amino-pyrazolo[1,5-a]pyrimidines 3 has been investigated. Heating a mixture of α-azidochalcones 1 and 3-aminopyrazoles 2 under the mild condition afforded desired compounds with a large substrate scope in good to excellent yields. All obtained products were evaluated as α-glucosidase inhibitors and exhibited excellent potency with IC50 values ranging from 15.2 ± 0.4 µM to 201.3 ± 4.2 µM. Among them, compound 3d was around 50-fold more potent than acarbose (IC50 = 750.0 ± 1.5 µM) as standard inhibitor. Regarding product structures, kinetic study and molecular docking were carried out for two of the most potent ones. © 2020, The Author(s).
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