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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

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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.

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]

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