Synthesis and biological activity evaluation of novel 3,5,7-trisubstituted pyrazolo[1,5-a]pyrimidines

Vlková, Kristýna; Padrtová, Růžena; Gucký, Tomáš; Peřina, Miroslav; Řezníčková, Eva; Kryštof, Vladimı́r

doi:10.1016/j.bmcl.2022.129096

Cited by 2 publications

(3 citation statements)

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“…For instance, there are a number of reports on the formation of regioisomeric 5-amino and 7-aminopyrazolo[1,5- a ]pyrimidines when 3-aminopyrazole interacts with arylidene cyanoacetic ether. 14 The construction of the pyrazolopyrimidine system is possible from 3-aminopyrazole and diethyl malonate, 2 5 9 acrylic 12 or cinnamic 13 acid esters. Copper-catalyzed coupling of aminopyrazole with 2-bromobenzoate allows for the synthesis of substituted derivatives of pyrazolochinazoline.…”

Section: Table 1 Content Of Pyrazolo[15- ...mentioning

confidence: 99%

“…The heterocyclic system of pyrazolo [3,4-b]pyrimidine serves as a carrier of a broad spectrum of biologically significant properties, providing its derivatives with a crucial role in modern pharmaceutical and medicinal chemistry. Specifically, the structural resemblance of pyrazolopyrimidines to purine bases explains their inhibitory effects on various enzymes, 1 including cyclin-dependent kinases (CDKs), 2,3 serine-threonine kinases (RIP), 4 tyrosine kinases (FLT), 5 KDR 3 kinases, proteases, 6 and polymerases. 7 This, in turn, enables the prediction of antitumor [2][3][4][5][6][7][8] and antiviral 9 activities of pyrazolopyrimidine derivatives.…”

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confidence: 99%

“…Specifically, the structural resemblance of pyrazolopyrimidines to purine bases explains their inhibitory effects on various enzymes, 1 including cyclin-dependent kinases (CDKs), 2,3 serine-threonine kinases (RIP), 4 tyrosine kinases (FLT), 5 KDR 3 kinases, proteases, 6 and polymerases. 7 This, in turn, enables the prediction of antitumor [2][3][4][5][6][7][8] and antiviral 9 activities of pyrazolopyrimidine derivatives. Additionally, the influence of pyrazolopyrimidines on serotonin, 10 ben-zodiazepine, 4 and glutamate 12 receptors has been discovered, correlating with their psychotropic 10 and anticonvulsant 12,13 effects.…”

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confidence: 99%

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Efficient Synthesis of Tetrahydropyrazolo[1,5-a]pyrimidines Based on the Recyclization of N-Arylitaconimides with Aminopyrazoles

Shmoylova,

Kovygin,

Shikhaliev

2024

Synthesis

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This article presents an efficient one-step synthesis of tetrahydropyrazolo[1,5-a]pyrimidines through the recyclization of N-arylitaconimides with aminopyrazoles. The heterocyclic system of pyrazolo[3,4-b]pyrimidine is known for its diverse biological properties, making its derivatives significant in pharmaceutical and medicinal chemistry. The study focuses on the regio- and chemoselective cascade reaction of N-arylitaconimides with 5-aminopyrazoles, demonstrating a new approach to synthesizing pyrazolo[1,5-a]pyrimidines and pyrazolo[3,4-b]pyridines. The methodology, involving boiling in isopropyl alcohol with acetic acid, yields selectively either pyrazolo[3,4-b]pyridines or pyrazolo[1,5-a]pyrimidines based on the substituents in the aminopyrazoles. The study elucidates the reaction mechanism, structural characterization using NMR spectroscopy, and confirms the structures via high-performance liquid chromatography and mass spectrometry. The simplicity and synthetic potential of this approach make it a valuable method for the preparation of these heterocyclic frameworks.

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Section: Table 1 Content Of Pyrazolo[15- ...mentioning

confidence: 99%