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Synthesis, Qsar Modeling, and Molecular Docking Studies of 1,2,3-Triazole-Pyrazole Hybrids As Significant Anti-Cancer and Anti-Microbial Agents Publisher



Tamardash LK1 ; Bakherad M1 ; Bakherad H2, 3 ; Jalali F2 ; Keivanloo A1 ; Mozafari Z1
Authors
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Authors Affiliations
  1. 1. Faculty of Chemistry, Shahrood University of Technology, Shahrood, 3619995161, Iran
  2. 2. Department of Pharmaceutical Biotechnology, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran
  3. 3. Isfahan Pharmaceutical Sciences Research Center, Isfahan University of Medical Sciences, Isfahan, Iran

Source: Journal of Molecular Structure Published:2025


Abstract

In this research, the synthesis of 1,2,3-triazoles-based pyrazole carbaldehyde via click reaction of 5-azido-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde with terminal alkynes catalyzed by Cu(OAc)2 is reported. The antimicrobial and anticancer activities of the synthesized compounds were evaluated against the three pathogenic microorganisms: E. coli, P. aeruginosa, and C. albicans; two cancer cell lines were MCF-7 and OVCAR3. Among the screened compounds, 4i possessed the most potential cytotoxic activity against MCF-7 cell lines with an IC50 of 0.101 ± 0.002 µM; in contrast, 4e showed a dual activity as it was highly potent against the OVCAR3 cell line, where the IC50 = 0.264 ± 0.0007 µM, and high antibacterial activity towards E. coli, MIC = 0.431 ± 0.009 µM. Moreover, high antifungal activity appeared in compound 4j against C. albicans with an MIC of 0.558 ± 0.01 µM. In addition, the performance of the constructed QSAR model was assessed through various statistical metrics. Notably, the coefficients of determination (R2) yielded a remarkable value of 0.99, signifying a high degree of correlation between the predicted and observed values. In addition, the mean absolute error (MAE) was found to be 0.014, further attesting to the robustness and predictive capability of the proposed model. Novel compounds were suggested as possible active inhibitors based on the established link within the suggested QSAR model. Molecular docking studies' ligand-receptor (LR) interactions were used to verify and assess the compounds' correctness. © 2025 Elsevier B.V.
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