Synthesis and Antifungal Properties of 1,2,4-Triazole Schiff Base Agents Based on a 3D-QSAR Model.
Chem Biodivers
; 21(5): e202302064, 2024 May.
Article
em En
| MEDLINE
| ID: mdl-38390665
ABSTRACT
Based on our previous research, a 3D-QSAR model (q2=0.51, ONC=5, r2=0.982, F=271.887, SEE=0.052) was established to predict the inhibitory effects of triazole Schiff base compounds on Fusarium graminearum, and its predictive ability was also confirmed through the statistical parameters. According to the results of the model design, 30 compounds with superior bioactivity compared to the template molecule 4 were obtained. Seven of these compounds (DES2-6, DES9-10) with improved biological activity and readily available raw materials were successfully synthesized. Their structures were confirmed through HRMS, NMR, and single crystal X-ray diffraction analysis (DES-5). The bioactivity of the final products was investigated through an inâ
vitro antifungal assay. There was little difference in the EC50 values between the experimental and predicted values of the model, demonstrating the reliability of the model. Especially, DES-3 (EC50=9.915â
mg/L) and DES-5 (EC50=9.384â
mg/L) exhibited better inhibitory effects on Fusarium graminearum compared to the standard drug (SD) triadimenol (EC50=10.820â
mg/L). These compounds could serve as potential new fungicides for future research. The interaction between the final products and isocitrate lyase (ICL) was investigated through molecular docking. Compounds with R groups that have a higher electron-donating capacity were found to be biologically active.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Bases de Schiff
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Triazóis
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Testes de Sensibilidade Microbiana
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Relação Quantitativa Estrutura-Atividade
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Fusarium
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Antifúngicos
Idioma:
En
Ano de publicação:
2024
Tipo de documento:
Article