Special Issue “Recent Advances in the Synthesis, Functionalization and Applications of Pyrazole-Type Compounds”

Silva, Vera L. M.; Silva, Artur M. S.

doi:10.3390/molecules26164989

Cited by 3 publications

(2 citation statements)

References 16 publications

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“…Pyrazole nucleus has been extensively investigated as pharmacophore [1][2][3][4][5][6][7][8][9][10][11] and several aminopyrazoles bearing a free amino group showed relevant biological activity in different therapeutic areas [12][13][14][15][16]. Specifically, 5-aminopyrazoles (5APs) have been deeply studied for their anti-inflammatory and anticancer activity [17,18], providing useful ligands for receptors or enzymes, as p38 MAPK [19][20][21][22], COX [23], carbonic anhydrase [24], and other different targets involved in cancer progression [25,26], as demonstrated by the recent approval of 5AP Pirtobrutinib, a reversible BTK inhibitor, clinically used for the treatment of mantle cell lymphoma (MCL) [27][28][29][30][31][32][33].…”

Section: Introductionmentioning

confidence: 99%

Investigations of Antioxidant and Anti-Cancer Activities of 5-Aminopyrazole Derivatives

Rapetti,

Spallarossa,

Russo

et al. 2024

Molecules

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To further extend the structure-activity relationships (SARs) of 5-aminopyrazoles (5APs) and identify novel compounds able to interfere with inflammation, oxidative stress, and tumorigenesis, 5APs 1–4 have been designed and prepared. Some chemical modifications have been inserted on cathecol function or in aminopyrazole central core; in detail: (i) smaller, bigger, and more lipophilic substituents were introduced in meta and para positions of catechol portion (5APs 1); (ii) a methyl group was inserted on C3 of the pyrazole scaffold (5APs 2); (iii) a more flexible alkyl chain was inserted on N1 position (5APs 3); (iv) the acylhydrazonic linker was moved from position 4 to position 3 of the pyrazole scaffold (5APs 4). All new derivatives 1–4 have been tested for radical scavenging (DPPH assay), anti-aggregating/antioxidant (in human platelets) and cell growth inhibitory activity (MTT assay) properties. In addition, in silico pharmacokinetics, drug-likeness properties, and toxicity have been calculated. 5APs 1 emerged to be promising anti-proliferative agents, able to suppress the growth of specific cancer cell lines. Furthermore, derivatives 3 remarkably inhibited ROS production in platelets and 5APs 4 showed interesting in vitro radical scavenging properties. Overall, the collected results further confirm the pharmaceutical potentials of this class of compounds and support future studies for the development of novel anti-proliferative and antioxidant agents.

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Section: Introductionmentioning

confidence: 99%

Investigations of Antioxidant and Anti-Cancer Activities of 5-Aminopyrazole Derivatives

Rapetti,

Spallarossa,

Russo

et al. 2024

Molecules

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“…Nitrogen-containing heterocyclic compounds are the world's major selling drugs 1 and many among the top ten most selling drugs contain N -containing heterocycles. 2 Among several N-heterocycles, azoles, in particular indazoles 1 a ,3 and pyrazoles, 1 b ,4 are important classes of compounds that are found in a variety of natural products and bio-active molecules (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Visible light-induced functionalization of indazole and pyrazole: a recent update

Ghosh¹,

Ghosh

et al. 2022

Chem. Commun.

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Supramolecular Assemblies in Pyridine- and Pyrazole-Based Coordination Compounds of Co(II) and Ni(II): Characterization, Hirshfeld Analysis and Theoretical Studies

et al. 2023

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Two new Ni(II) and Co(II) coordination compounds,viz., [Ni(H2O)5(DMAP)](IPhth)·2H2O (1) and [Co(Hdmpz)4(H2O)2]Cl2 (2) (where DMAP = 4-dimethylaminopyridine, IPhth = Isophthalate, Hdmpz = 3,5-dimethylpyrazole),were synthesized and characterized using elemental analysis, TGA, spectroscopic (FTIR and electronic) and single-crystal X-ray diffraction techniques. Compound 1 crystallizes as a co-crystal hydrate of Ni(II), whereas compound 2 is a mononuclear compound of Co(II). The crystal structure analysis of compound 1 reveals the presence of various non-covalent interactions such as anion‒π, π‒π, C‒H∙∙∙π, C‒H∙∙∙C, etc., which stabilize the layered assembly of the compound. In compound 2, enclathration of counter chloride ions within the supramolecular trimeric host cavity plays a crucial role in the stabilization of the compound. The non-covalent interactions observed in the crystal structures were further studied theoretically, focusing on the cooperative π-stacking interactions between the DMAP and IPhth counter-ions in 1. To identify the non-covalent interactions of the compounds, Hirshfeld surfaces and their associated two-dimensional fingerprint regions were analyzed. Theoretical calculations confirm that H-bonding interactions combined with the π-stacking contacts are crucial synthons for the solid-state stability of compound 1.

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Special Issue “Recent Advances in the Synthesis, Functionalization and Applications of Pyrazole-Type Compounds”

Abstract: Pyrazoles and their reduced form, pyrazolines, are considered privileged scaffolds in medicinal chemistry, owing to their remarkable biological activities, physicochemical properties and occurrence in many low-molecular-weight compounds present in several marketed drugs (e [...]

Cited by 3 publications

References 16 publications

Investigations of Antioxidant and Anti-Cancer Activities of 5-Aminopyrazole Derivatives

Investigations of Antioxidant and Anti-Cancer Activities of 5-Aminopyrazole Derivatives

Visible light-induced functionalization of indazole and pyrazole: a recent update

Supramolecular Assemblies in Pyridine- and Pyrazole-Based Coordination Compounds of Co(II) and Ni(II): Characterization, Hirshfeld Analysis and Theoretical Studies

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