Unknown

Dataset Information

0

An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with ?-glucosidase inhibitory activity.

ABSTRACT: In an attempt to find novel ?-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 ?-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 ?-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.

SUBMITTER: Peytam F 

PROVIDER: S-EPMC7018746 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity.

Peytam Fariba F   Adib Mehdi M   Shourgeshty Reihaneh R   Firoozpour Loghman L   Rahmanian-Jazi Mahmoud M   Jahani Mehdi M   Moghimi Setareh S   Divsalar Kouros K   Faramarzi Mohammad Ali MA   Mojtabavi Somayeh S   Safari Fatemeh F   Mahdavi Mohammad M   Foroumadi Alireza A  

Scientific reports 20200213 1

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 IC<sub>50</sub> values rang  ...[more]

Similar Datasets

Unknown Exploration of Pyrazolo[1,5-a]pyrimidines as Membrane-Bound Pyrophosphatase Inhibitors.
| S-EPMC8597055 | biostudies-literature
Unknown Discovery of 3-(4-sulfamoylnaphthyl)pyrazolo[1,5-a]pyrimidines as potent and selective ALK2 inhibitors.
| S-EPMC6218249 | biostudies-literature
Unknown Green one pot solvent-free synthesis of pyrano[2,3-c]-pyrazoles and pyrazolo[1,5-a]pyrimidines.
| S-EPMC6257727 | biostudies-literature
Unknown Palladium-Catalyzed Intramolecular Cross-Dehydrogenative Coupling: Synthesis of Fused Imidazo[1,2-<i>a</i>]pyrimidines and Pyrazolo[1,5-<i>a</i>]pyrimidines.
| S-EPMC6641030 | biostudies-literature
Unknown Synthesis and biological evaluation of chalcone-linked pyrazolo[1,5-<i>a</i>]pyrimidines as potential anticancer agents.
| S-EPMC6084153 | biostudies-literature
Unknown Catalyst-Switchable Regiocontrol in the Direct Arylation of Remote C-H Groups in Pyrazolo[1,5-a]pyrimidines.
| S-EPMC4531820 | biostudies-literature
Unknown Microwave-Assisted Sequential One-Pot Synthesis of 8-Substituted Pyrazolo[1,5-a][1,3,5]triazines.
| S-EPMC8230123 | biostudies-literature
Unknown Biological Evaluation and Molecular Docking with In Silico Physicochemical, Pharmacokinetic and Toxicity Prediction of Pyrazolo[1,5-a]pyrimidines.
| S-EPMC7144935 | biostudies-literature
Unknown Design, synthesis, molecular docking, and in vitro α-glucosidase inhibitory activities of novel 3-amino-2,4-diarylbenzo[4,5]imidazo[1,2-a]pyrimidines against yeast and rat α-glucosidase.
| S-EPMC8184976 | biostudies-literature
Unknown Discovery of Imidazo[1,2-a]pyrazines and Pyrazolo[1,5-c]pyrimidines as TARP γ-8 Selective AMPAR Negative Modulators.
| S-EPMC6421542 | biostudies-literature