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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
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Authors Affiliations
  1. 1. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
  2. 2. Department of Medicinal Chemistry, Faculty of Pharmacy and The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Neuroscience Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences, Kerman, Iran
  4. 4. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Department of Biology, Faculty of Science, University of Guilan, Rasht, Iran
  6. 6. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

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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