Novel arylazopyrazole inhibitors of cyclin-dependent kinases

Jorda, Radek; Schütznerová, Eva; Cankař, Petr; Brychtová, Veronika; Navrátilová, Jana; Kryštof, Vladimı́r

doi:10.1016/j.bmc.2015.03.025

Cited by 18 publications

(7 citation statements)

References 30 publications

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“…144-146°C. 1 Table 2. The corresponding pyrazole 1 (1.0 mmol), boronic acid 2 (2.0 mmol), potassium carbonate (0.272 g, 2.0 mmol), and XPhos (0.009 g, 0.020 mmol) were weighed into a pressure tube.…”

Section: N-(4-chloro-1-methyl-3-phenyl-1h-pyrazol-5-yl)acetamide (1d)mentioning

confidence: 99%

4‐Arylation of N‐Acylamino‐ and Aminopyrazoles by the Suzuki–Miyaura Cross‐Coupling Reaction

Jedinák

Cankař

2016

Eur J Org Chem

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Halogenated aminopyrazoles have rarely been utilized in metal-catalysed cross-coupling reactions mainly due to the complexation of the aminopyrazoles to the metal center, which deactivates the catalyst. In this paper we reveal that the appropriate combination of palladium source and ligand enables efficient Suzuki-Miyaura cross-coupling reactions with even challenging substrates such as halogenated aminopyrazoles. The combination of Pd(OAc) 2 and XPhos allowed effi-

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Section: N-(4-chloro-1-methyl-3-phenyl-1h-pyrazol-5-yl)acetamide (1d)mentioning

confidence: 99%

4‐Arylation of N‐Acylamino‐ and Aminopyrazoles by the Suzuki–Miyaura Cross‐Coupling Reaction

Jedinák

Cankař

2016

Eur J Org Chem

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“…For the subclass of hydrazonodiaminopyrazole-type compounds, Kojic et al have demonstrated how 4-(4-fluoro-3trifluoromethylphenyl)hydrazono 4H-pyrazole-3,5-diamine displays an anti-inflammatory effect through integrin-linked kinase inhibition 54,55 . Moreover, Kryštof et al identified the compound 4-[(3,5-diamino-1H-pyrazol-4-yl)diazenyl]phenol as a selective inhibitor of cyclin-dependent kinase 9 (CDK9) in vitro 56,57 . CDK enzymes play essential roles in the regulation of cell division in humans and as such, the development of specific CDK inhibitors may result in novel anticancer agents.…”

Section: Discussionmentioning

confidence: 99%

Identification of small molecules that interfere with c-di-GMP signaling and induce dispersal of Pseudomonas aeruginosa biofilms

Andersen

Hultqvist

Jansen

et al. 2021

npj Biofilms Microbiomes

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Microbial biofilms are involved in a number of infections that cannot be cured, as microbes in biofilms resist host immune defenses and antibiotic therapies. With no strict biofilm-antibiotic in the current pipelines, there is an unmet need for drug candidates that enable the current antibiotics to eradicate bacteria in biofilms. We used high-throughput screening to identify chemical compounds that reduce the intracellular c-di-GMP content in Pseudomonas aeruginosa. This led to the identification of a small molecule that efficiently depletes P. aeruginosa for c-di-GMP, inhibits biofilm formation, and disperses established biofilm. A combination of our lead compound with standard of care antibiotics showed improved eradication of an implant-associated infection established in mice. Genetic analyses provided evidence that the anti-biofilm compound stimulates the activity of the c-di-GMP phosphodiesterase BifA in P. aeruginosa. Our work constitutes a proof of concept for c-di-GMP phosphodiesterase-activating drugs administered in combination with antibiotics as a viable treatment strategy for otherwise recalcitrant infections.

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“…Its IC 50 values are 67.4, 37.7, and 50 µM, respectively. It was further investigated for ability to induce apoptosis, and it happened in RPMI-8226 multiple myeloma cell line only [ 32 ].…”

Section: Pyrazole-based Cyclin-dependent Kinase Inhibitorsmentioning

confidence: 99%

Evaluation of Substituted Pyrazole-Based Kinase Inhibitors in One Decade (2011–2020): Current Status and Future Prospects

et al. 2022

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Pyrazole has been recognized as a pharmacologically important privileged scaffold whose derivatives produce almost all types of pharmacological activities and have attracted much attention in the last decades. Of the various pyrazole derivatives reported as potential therapeutic agents, this article focuses on pyrazole-based kinase inhibitors. Pyrazole-possessing kinase inhibitors play a crucial role in various disease areas, especially in many cancer types such as lymphoma, breast cancer, melanoma, cervical cancer, and others in addition to inflammation and neurodegenerative disorders. In this article, we reviewed the structural and biological characteristics of the pyrazole derivatives recently reported as kinase inhibitors and classified them according to their target kinases in a chronological order. We reviewed the reports including pyrazole derivatives as kinase inhibitors published during the past decade (2011–2020).

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Novel arylazopyrazole inhibitors of cyclin-dependent kinases

Cited by 18 publications

References 30 publications

4‐Arylation of N‐Acylamino‐ and Aminopyrazoles by the Suzuki–Miyaura Cross‐Coupling Reaction

4‐Arylation of N‐Acylamino‐ and Aminopyrazoles by the Suzuki–Miyaura Cross‐Coupling Reaction

Identification of small molecules that interfere with c-di-GMP signaling and induce dispersal of Pseudomonas aeruginosa biofilms

Evaluation of Substituted Pyrazole-Based Kinase Inhibitors in One Decade (2011–2020): Current Status and Future Prospects

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