Green Synthesis and Antifungal Activities of Novel N-Aryl Carbamate Derivatives
Abstract
1. Introduction
2. Results
2.1. Chemistry
2.2. In Vitro Antifungal Activity
3. Discussion
4. Materials and Methods
4.1. General Information
4.2. Synthetic Procedures
4.2.1. Synthesis of Amides 3
4.2.2. Synthesis of Carbamates 1
4.3. Bioassays
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | Average Inhibition Rate ± SD (%) (n = 3) a | ||||||
---|---|---|---|---|---|---|---|
No. | B. c. | M. o. | P. a. | F. g. | V. m. | C. s. | F. o. |
1a | 0 | 0.44 ± 1.38 | 2.96 ± 3.35 | 16.86 ± 1.76 | 2.36 ± 2.9 | 11.92 ± 9.83 | 25.2 ± 0.92 |
1b | 1.33 ± 1.52 | 3.31 ± 7.28 | 3.27 ± 2.15 | 4.98 ± 0.64 | 9.36 ± 0.83 | 9.09 ± 0.71 | 25.32 ± 1.56 |
1c | 18.42 ± 2.46 | 12.67 ± 1.38 | 27.86 ± 1.4 | 37.16 ± 0.81 | 31.24 ± 0.93 | 20.05 ± 0.53 | 31.24 ± 8.07 |
1d | 42.58 ± 1.72 | 43.46 ± 0.28 | 43.14 ± 0.67 | 51.58 ± 0.72 | 52.94 ± 1.19 | 29.1 ± 1.62 | 42.03 ± 0.49 |
1e | 13.32 ± 3.08 | 11.22 ± 0.29 | 16.68 ± 2.73 | 22.4 ± 3.46 | 13.47 ± 5.24 | 15.71 ± 0.73 | 27.66 ± 1.64 |
1f | 55.98 ± 2.19 | 53.03 ± 0.85 | 55.77 ± 1.24 | 64.1 ± 2.2 | 68.91 ± 1.56 | 41.1 ± 1.29 | 43.26 ± 1.09 |
1g | 0 | 0 | 0 | 0.88 ± 0.94 | 3.15 ± 2.95 | 11.88 ± 8.81 | 27.03 ± 1.79 |
1h | 64.44 ± 0.95 | 64.82 ± 1.15 | 64.33 ± 0.81 | 54.27 ± 0.66 | 61.69 ± 0.77 | 24.79 ± 1.35 | 20.46 ± 0.28 |
1i | 10.52 ± 1.79 | 7.79 ± 1.57 | 15.9 ± 1.69 | 39.17 ± 2.39 | 24.73 ± 1.29 | 18.65 ± 1.62 | 18.69 ± 7.94 |
1j | 32.70 ± 1.37 | 28.77 ± 0.87 | 29.93 ± 1.34 | 45.89 ± 1.58 | 37.38 ± 1.57 | 37.07 ± 0.99 | 42.09 ± 0.71 |
1k | 4.09 ± 0.68 | 0 | 4.33 ± 1.33 | 4.6 ± 0.83 | 6.82 ± 1 | 23.22 ± 1.65 | 20.74 ± 1.01 |
1l | 43.64 ± 1.59 | 40.56 ± 0.75 | 49.18 ± 2 | 56.44 ± 1.63 | 42.43 ± 1.14 | 47.72 ± 0.93 | 36.78 ± 1.04 |
1m | 57.94 ± 0.73 | 52.05 ± 1.16 | 49.64 ± 4.23 | 52.52 ± 0.82 | 34.78 ± 1.35 | 30.01 ± 0.99 | 26.55 ± 0.51 |
1n | 0 | 0 | 3.27 ± 2.7 | 13.25 ± 1.75 | 0 | 0 | 25.84 ± 1.02 |
1o | 7.12 ± 0.86 | 1.33 ± 1.33 | 0.11 ± 0.65 | 0 | 0 | 0 | 0 |
1p | 5.28 ± 3.11 | 0 | 0 | 16.73 ± 22.9 | 7.53 ± 7.73 | 0.89 ± 4.54 | 1.25 ± 0.48 |
1q | 0 | 0 | 14.6 ± 2.24 | 22.25 ± 4.3 | 5.01 ± 4.77 | 2.6 ± 6.49 | 0 |
1r | 0.6 ± 2.45 | 0 | 0.22 ± 0.8 | 0 | 0 | 0 | 3.31 ± 1.26 |
1s | 55.76 ± 1.26 | 55.16 ± 1.32 | 60.37 ± 3.15 | 53.41 ± 3.88 | 52.08 ± 0.56 | 52.67 ± 1.35 | 59.07 ± 3.2 |
1t | 71.93 ± 1.74 | 74.18 ± 0.58 | 69.96 ± 3.93 | 93.61 ± 0.21 | 70.72 ± 0.43 | 69.97 ± 1.86 | 67.89 ± 0.28 |
1u | 13.05 ± 2.42 | 13.12 ± 1.06 | 14.05 ± 0.34 | 36.79 ± 0.35 | 16.09 ± 0.56 | 6.98 ± 2.58 | 18.22 ± 1.25 |
1v | 25.57 ± 1.42 | 29.71 ± 3.35 | 36.6 ± 0.51 | 28.15 ± 0.93 | 23.03 ± 1.9 | 20.38 ± 1.52 | 33.14 ± 0.48 |
1w | 67.49 ± 1.58 | 67.49 ± 0.67 | 69.78 ± 1.62 | 49.82 ± 2.84 | 71.99 ± 0.42 | 65.22 ± 1.69 | 56.92 ± 0.96 |
1x | 70.16 ± 1.52 | 70.25 ± 0.65 | 72.48 ± 0.12 | 48.89 ± 2.01 | 72.06 ± 0.52 | 68.08 ± 1.62 | 61.92 ± 0.42 |
1y | 47.88 ± 0.81 | 54.82 ± 1.34 | 57.02 ± 0.6 | 74.55 ± 1.18 | 53.1 ± 0.23 | 43.13 ± 2.77 | 52.73 ± 0.21 |
1z | 61.42 ± 0.49 | 63.38 ± 0.63 | 64.12 ± 0.46 | 77.6 ± 2.6 | 73.77 ± 1.21 | 58.76 ± 0.6 | 66.35 ± 0.55 |
1aa | 27.31 ± 0.76 | 32.29 ± 1.29 | 32.28 ± 0.35 | 46.44 ± 0.49 | 38.05 ± 0.79 | 22.23 ± 0.82 | 32.12 ± 0.95 |
1ab | 6.77 ± 0.41 | 3.03 ± 0.45 | 7.35 ± 0.54 | 19.8 ± 4.98 | 5.48 ± 0.47 | 0.26 ± 0.44 | 6.92 ± 1.77 |
1ac | 54.48 ± 0.57 | 54.67 ± 0.6 | 55.51 ± 1.14 | 77.85 ± 4.53 | 55.12 ± 0.3 | 51.3 ± 0.61 | 40.86 ± 0.73 |
1ad | 44.31 ± 0.24 | 46.56 ± 1.14 | 47.3 ± 0.56 | 70.07 ± 0.57 | 46.4 ± 0.13 | 40.42 ± 0.25 | 24.15 ± 4.07 |
1ae | 31.89 ± 0.75 | 31.73 ± 1.15 | 30.76 ± 1.02 | 55.45 ± 1.42 | 36.96 ± 1.34 | 27.13 ± 0.81 | 11.8 ± 0.55 |
1af | 49.05 ± 0.45 | 52.80 ± 0.58 | 50.00 ± 0.69 | 85.83 ± 1.55 | 52.73 ± 1.75 | 45.51 ± 0.51 | 34.03 ± 0.82 |
1ag | 73.94 ± 0.61 | 72.72 ± 0.96 | 75.4 ± 0.45 | 73.37 ± 2.76 | 76.78 ± 0.47 | 72.12 ± 0.66 | 68.42 ± 0.48 |
1ah | 62.07 ± 0.54 | 55.04 ± 0.14 | 61.56 ± 1.01 | 69.09 ± 0.88 | 63.91 ± 1.05 | 56.09 ± 4.16 | 50.58 ± 0.95 |
1ai | 10.05 ± 0.67 | 5.67 ± 1.1 | 19.67 ± 6.49 | 16.77 ± 7.16 | 6.24 ± 1.73 | 16.49 ± 1.17 | 11.1 ± 0.89 |
AZO | 54.39 ± 0.24 | 59.94 ± 0.24 | 56.40 ± 0.87 | 58.17 ± 0.22 | 63.14 ± 0.66 | 54.79 ± 0.67 | 62.50 ± 2.14 |
Compound | Regression Equation | R2 | EC50 (μg/mL, 95% CI) a | EC50 (μM, 95% CI) a |
---|---|---|---|---|
B. cinerea | ||||
1t | Y = 2.04x + 1.86 | 0.972 | 34.05 (32.25–42.39) | 0.1548 (0.1466–0.1927) |
1x | Y = 2.89x + 0.48 | 0.994 | 36.55 (31.91–40.25) | 0.1498 (0.1308–0.1650) |
1ag | Y = 2.41x + 1.15 | 0.974 | 29.44 (25.66–34.33) | 0.1141 (0.0995–0.1331) |
azoxystrobin | Y = 0.38x + 4.52 | 0.917 | 18.06 (4.97–37.44) | 0.0448 (0.0123–0.0928) |
M. grisea | ||||
1t | Y = 1.65x + 2.62 | 0.998 | 27.34 (24.54–34.22) | 0.1243 (0.1115–0.1555) |
1x | Y = 2.60x + 0.98 | 0.995 | 34.53 (32.70–40.98) | 0.1415 (0.1340–0.1680) |
1ag | Y = 2.03x + 1.99 | 0.997 | 29.98 (27.23–36.05) | 0.1162 (0.1055–0.1397) |
azoxystrobin | Y = 0.32x + 4.70 | 0.917 | 7.90 (0.08–17.84) | 0.0196 (0.0002–0.0443) |
P. aphanidermatum | ||||
1x | Y = 2.22x + 1.73 | 0.974 | 29.22 (27.04–35.04) | 0.1198 (0.1108–0.1436) |
1ag | Y = 1.95x + 2.27 | 0.993 | 24.64 (20.27–27.40) | 0.0955 (0.0503–0.1062) |
azoxystrobin | Y = 0.33x + 4.61 | 0.968 | 13.99 (1.08–30.50) | 0.0347 (0.0027–0.0757) |
F. graminearum | ||||
1t | Y = 2.42x + 1.83 | 0.955 | 20.22 (13.71–30.14) | 0.0919 (0.0623–0.1370) |
1ac | Y = 2.23x + 2.03 | 0.977 | 21.17 (19.31–25.15) | 0.0850 (0.0776–0.1010) |
1af | Y = 1.78x + 3.04 | 0.993 | 12.50 (10.38–14.93) | 0.0413 (0.0343–0.0493) |
azoxystrobin | Y = 0.34x + 4.65 | 0.971 | 10.36 (0.48–21.80) | 0.0257 (0.0012–0.0541) |
V. mali | ||||
1t | Y = 1.80x + 2.35 | 0.989 | 28.96 (25.63–34.98) | 0.1316 (0.1165–0.1590) |
1w | Y = 2.45x + 1.52 | 0.902 | 26.23 (13.61–53.10) | 0.1075 (0.0558–0.2176) |
1x | Y = 2.24x + 1.75 | 0.993 | 27.87 (25.61–33.17) | 0.1142 (0.1050–0.1359) |
1ag | Y = 2.06x + 2.05 | 0.991 | 26.69 (23.65–31.17) | 0.1034 (0.0917–0.1208) |
azoxystrobin | Y = 0.5x + 4.42 | 0.958 | 4.71 (0.06–11.32) | 0.0117 (0.0002–0.0281) |
F. oxysporum | ||||
1t | Y = 1.74x + 2.42 | 0.975 | 30.03 (28.35–38.60) | 0.1365 (0.1289–0.1755) |
1z | Y = 0.94x + 3.84 | 0.885 | 16.65 (5.71–38.79) | 0.0553 (0.0188–0.1288) |
1ag | Y = 1.74x + 2.63 | 0.996 | 22.71 (21.29–29.07) | 0.0880 (0.0825–0.1127) |
azoxystrobin | Y = 0.50x + 4.42 | 0.977 | 14.14 (5.66–23.54) | 0.0351 (0.0140–0.0584) |
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Liu, X.; Sun, Y.; Liu, L.; Duan, X.; You, S.; Yu, B.; Pan, X.; Guan, X.; Lin, R.; Song, L. Green Synthesis and Antifungal Activities of Novel N-Aryl Carbamate Derivatives. Molecules 2024, 29, 3479. https://doi.org/10.3390/molecules29153479
Liu X, Sun Y, Liu L, Duan X, You S, Yu B, Pan X, Guan X, Lin R, Song L. Green Synthesis and Antifungal Activities of Novel N-Aryl Carbamate Derivatives. Molecules. 2024; 29(15):3479. https://doi.org/10.3390/molecules29153479
Chicago/Turabian StyleLiu, Xiyao, Yuyao Sun, Lifang Liu, Xufei Duan, Shujun You, Baojia Yu, Xiaohong Pan, Xiong Guan, Ran Lin, and Liyan Song. 2024. "Green Synthesis and Antifungal Activities of Novel N-Aryl Carbamate Derivatives" Molecules 29, no. 15: 3479. https://doi.org/10.3390/molecules29153479
APA StyleLiu, X., Sun, Y., Liu, L., Duan, X., You, S., Yu, B., Pan, X., Guan, X., Lin, R., & Song, L. (2024). Green Synthesis and Antifungal Activities of Novel N-Aryl Carbamate Derivatives. Molecules, 29(15), 3479. https://doi.org/10.3390/molecules29153479