Synthesis of new 4,4'-(1H-1,2,3-triazole)-bis(1H-pyrazol-5-ols) and prospects for their study as potential antitumor agents

Authors

DOI:

https://doi.org/10.15587/2519-4852.2025.327116

Keywords:

1,2,3-triazole, pyrazole, synthesis, anticancer activity, docking studies

Abstract

The aim of our work is to develop an efficient synthesis of a series of novel 4,4'-(1H-1,2,3-triazol)bis(1H-pyrazol-5-ols), synthesize the target substances, and perform molecular docking focusing on the interaction of the synthesized compounds with the active sites of known cytostatics targeting various stages of oncogenesis.

Materials and methods. The structure and purity of the obtained substances were confirmed by 1H NMR spectroscopy, 13C NMR spectroscopy and LC/MS. Docking studies were performed for the substances synthesized using Autodock 4.2 software.

Results and discussion. A series of novel 4,4'-(1H-1,2,3-triazol)bis(1H-pyrazol-5-ols) were synthesized via a tandem Knoevenagel–Michael reaction from two equivalents of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one with various 1,2,3-triazole aldehydes catalyzed by ammonium acetate in ethanol in high yields. As a result of the analysis of the array of docking computations and a detailed analysis of the geometric arrangement in the active sites of tumour targets (C-abl kinase, deoxycytidine kinase (dCK), CSF1 receptor, EGFRK receptor, FOLR2 receptor, it was found that the synthesized derivatives may have antitumor effects through the mechanism of inhibition of the EGFRK receptor.

Conclusions. According to the molecular docking data, the newly synthesized derivatives 4,4'-((1H-1,2,3-triazol-4-yl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) may have an antitumor effect through the mechanism of EGFRK receptor inhibition

Supporting Agency

  • This project has received funding through the MSCA4 Ukraine project, which is funded by the European Union.

Author Biographies

Anna Geleverya, University of Chemistry and Technology Prague; V. N. Karazin Kharkiv National University

PhD Student

Department of Organic Chemistry

Department of Organic Chemistry

Anton Semenets, BAYER Limited Liability Company

PhD, Medical Representative

Sergiy М. Kovalenko, V. N. Karazin Kharkiv National University

Doctor of Chemical Sciences, Professor

Department of Organic Chemistry

Marharyta Suleiman, National University of Pharmacy

PhD, Associate Professor

Department of Medicinal Chemistry

Illya Podolsky, National University of Pharmacy

Doctor of Pharmaceutical Sciences, Professor

Department of Clinical Pharmacology

Lina Perekhoda, National University of Pharmacy

Doctor of Pharmaceutical Science, Professor

Department of Pharmaceutical Chemistry

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Synthesis of new 4,4'-(1H-1,2,3-triazole)-bis(1H-pyrazol-5-ols) and prospects for their study as potential antitumor agents

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Published

2025-04-30

How to Cite

Geleverya, A., Semenets, A., Kovalenko S. М., Suleiman, M., Podolsky, I., & Perekhoda, L. (2025). Synthesis of new 4,4’-(1H-1,2,3-triazole)-bis(1H-pyrazol-5-ols) and prospects for their study as potential antitumor agents. ScienceRise: Pharmaceutical Science, (2 (54), 49–58. https://doi.org/10.15587/2519-4852.2025.327116

Issue

No. 2 (54) (2025)

Section

Pharmaceutical Science

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Copyright (c) 2025 Anna Geleverya, Anton Semenets, Sergiy М. Kovalenko, Marharyta Suleiman, Illya Podolsky, Lina Perekhoda

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