Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety
Abstract
:1. Introduction
2. Result and Discussion
2.1. Chemistry
2.2. Antifungal Activity
3. Materials and Methods
3.1. Reagents and Analysis
3.2. Phytopathogenic Fungi
3.3. Synthesis
3.3.1. General Procedure for the Preparation of Intermediates B
3.3.2. General Procedure for the Preparation of Intermediates C
3.3.3. General Procedure for the Preparation of Intermediates D
3.3.4. Preparation Procedure of the Target Compounds E1–E45
3.4. Antifungal Bioassay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Compound | Mean Inhibition Rate ± SD (%) (n = 3) | |||
---|---|---|---|---|
M. oa | C. c | B. m | S. s | |
E1 | <10 | 29.19 ± 2.49 | <10 | 15.98 ± 0.82 |
E2 | <10 | 21.14 ± 0.9 | <10 | 31.66 ± 0.35 |
E3 | <10 | 19.46 ± 0.65 | <10 | 38.17 ± 0.91 |
E4 | 88.25 ± 0.17 | 60.74 ± 0.23 | 29.51 ± 0.95 | 22.78 ± 0.4 |
E5 | 25.2 ± 1.08 | 24.83 ± 2.42 | 12.5 ± 1.7 | 37.57 ± 1.91 |
E6 | <10 | <10 | <10 | 38.17 ± 0.91 |
E7 | <10 | 19.46 ± 0.47 | <10 | 15.38 ± 1.78 |
E8 | <10 | 16.44 ± 2.61 | <10 | 22.49 ± 0.46 |
E9 | 15.94 ± 1.6 | 16.78 ± 0.54 | <10 | 27.81 ± 1.33 |
E10 | 85.75 ± 0.8 | 66.44 ± 2.28 | <10 | 34.32 ± 0.62 |
E11 | 78.63 ± 0.76 | 68.12 ± 1.71 | 19.44 ± 0.64 | 21.89 ± 1.25 |
E12 | 21.99 ± 2.86 | 10.4 ± 1.56 | <10 | 28.4 ± 1.47 |
E13 | <10 | 10.74 ± 2.03 | <10 | 12.13 ± 0.45 |
E14 | 84.00 ± 2.86 | 44.3 ± 1.63 | 22.92 ± 0.24 | 15.38 ± 1.78 |
E15 | 71.41 ± 2.15 | <10 | 17.36 ± 0.63 | 17.46 ± 1.82 |
E16 | 64.35 ± 1.41 | 28.52 ± 2.06 | 12.85 ± 0.49 | 19.82 ± 1.28 |
E17 | 81.40 ± 0.34 | 33.22 ± 2.79 | 13.89 ± 1.45 | 23.08 ± 0.12 |
E18 | <10 | <10 | 12.85 ± 0.49 | 15.68 ± 1.37 |
E19 | <10 | 11.07 ± 2.59 | <10 | 35.5 ± 1.45 |
E20 | 74.16 ± 2.25 | 52.01 ± 0.88 | 15.63 ± 0.16 | <10 |
E21 | <10 | <10 | 13.89 ± 2.9 | 20.12 ± 2.76 |
E22 | 56.01 ± 1.49 | 28.19 ± 1.87 | 15.97 ± 2.45 | 21.6 ± 0.47 |
E23 | 80.12 ± 0.87 | 37.25 ± 0.83 | <10 | <10 |
E24 | <10 | 18.12 ± 5.12 | 12.85 ± 0.49 | <10 |
E25 | <10 | 11.07 ± 1.01 | 11.11 ± 1.21 | <10 |
E26 | 90.74 ± 0.74 | 68.12 ± 1.27 | 30.21 ± 1.77 | 18.64 ± 0.81 |
E27 | 83.32 ± 0.76 | 45.64 ± 0.31 | 26.04 ± 0.77 | 25.15 ± 2.6 |
E28 | <10 | 19.46 ± 1.27 | 22.22 ± 2.24 | <10 |
E29 | <10 | <10 | 13.54 ± 0.14 | <10 |
E30 | <10 | <10 | <10 | 14.2 ± 1.84 |
E31 | <10 | 24.5 ± 2.4 | 18.40 ± 3.18 | 15.09 ± 0.82 |
E32 | 69.03 ± 1.23 | 28.19 ± 1.15 | 24.31 ± 1.93 | <10 |
E33 | <10 | <10 | 16.32 ± 2 | <10 |
E34 | <10 | <10 | 20.49 ± 1.22 | 14.2 ± 1.57 |
E35 | <10 | <10 | 12.5 ± 1.7 | 34.62 ± 0.9 |
E36 | <10 | <10 | 14.93 ± 1.49 | <10 |
E37 | <10 | 21.81 ± 2.95 | 17.71 ± 1.23 | 22.49 ± 1.99 |
E38 | <10 | <10 | 10.76 ± 0.61 | <10 |
E39 | <10 | <10 | 11.11 ± 1.53 | 45.56 ± 1.16 |
E40 | <10 | <10 | 14.93 ± 2.07 | 28.7 ± 1.25 |
E41 | 66.90 ± 1.53 | 31.54 ± 1.09 | 15.28 ± 1.5 | <10 |
E42 | <10 | <10 | <10 | <10 |
E43 | <10 | 20.47 ± 2.2 | <10 | <10 |
E44 | <10 | <10 | <10 | 35.5 ± 1.62 |
E45 | 15.73 ± 0.56 | <10 | 13.89 ± 3.13 | <10 |
Thiasporine A | <10 | <10 | 10.76 ± 1.48 | 16.27 ± 1.44 |
IPTb | 91.81 ± 0.72 | 35.57 ± 1.34 | <10 | 75.15 ± 1.48 |
PCAc | 44.79 ± 1.38 | 46.98 ± 0.89 | 81.94 ± 1.65 | 97.63 ± 0.57 |
Compound | Regression Equation | R | EC50 (μg/mL) | 95% Confidence Interval (μg/mL) |
---|---|---|---|---|
E4 | y = 4.4560 + 2.4582x | 0.99 | 1.66 | 1.4621~1.8953 |
E10 | y = 4.8513 + 1.2331x | 0.98 | 2.01 | 1.5059~2.6873 |
E14 | y = 4.1548 + 2.3913x | 0.99 | 2.26 | 2.0124~2.5302 |
E17 | y = 4.7745 + 1.3753x | 0.98 | 1.45 | 1.1513~1.8211 |
E23 | y = 4.8359 + 0.9221x | 0.99 | 1.50 | 1.1483~1.9762 |
E26 | y = 4.7570 + 2.1660x | 0.99 | 1.29 | 1.1741~1.4018 |
E27 | y = 4.2101 + 1.8652x | 0.98 | 2.65 | 2.2483~3.1269 |
IPTa | y = 4.6250 + 1.0746x | 0.99 | 3.22 | 2.8494~3.6391 |
PCAb | y = 1.6473 + 2.2696x | 0.99 | 27.87 | 26.5822~29.2249 |
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Tian, Y.; Shi, J.; Deng, X.; Yu, T.; Hu, Y.; Hu, R.; Lei, Y.; Yu, L.; Zhu, X.; Li, J. Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety. Molecules 2023, 28, 7084. https://doi.org/10.3390/molecules28207084
Tian Y, Shi J, Deng X, Yu T, Hu Y, Hu R, Lei Y, Yu L, Zhu X, Li J. Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety. Molecules. 2023; 28(20):7084. https://doi.org/10.3390/molecules28207084
Chicago/Turabian StyleTian, Yao, Jinchao Shi, Xiaoqian Deng, Tingyu Yu, Yong Hu, Richa Hu, Yufeng Lei, Linhua Yu, Xiang Zhu, and Junkai Li. 2023. "Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety" Molecules 28, no. 20: 7084. https://doi.org/10.3390/molecules28207084
APA StyleTian, Y., Shi, J., Deng, X., Yu, T., Hu, Y., Hu, R., Lei, Y., Yu, L., Zhu, X., & Li, J. (2023). Design, Synthesis, and Antifungal Activity of Some Novel Phenylthiazole Derivatives Containing an Acylhydrazone Moiety. Molecules, 28(20), 7084. https://doi.org/10.3390/molecules28207084