Synthesis and Broad-Spectrum Antiviral Activity of Some Novel Benzo-Heterocyclic Amine Compounds
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biological Evaluation
2.2.1. Anti-influenza Virus Activity
NO. | Influenza A/hanfang/359/95 | Cox B3 | HCV | HBV | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
TC50 (μM) | IC50 (μM) | SI | TC50 (μM) | IC50 (μM) | SI | TC50 (μM) | IC50 (μM) | SI | TC50 (μM) | IC50 (μM) | SI | |
1a | 3.35 | >1.60 | - | 8.34 | 4.79 | 1.7 | 15.88 | 1.40 | 11.3 | 8.02 | 1.44 | 5.6 |
1b | 2.86 | >1.65 | - | 8.61 | 2.86 | 3.0 | NT | NT | NT | 3.21 | >1.85 | - |
1c | 4.52 | >0.66 | - | 25.15 | 1.93 | 13.0 | 46.78 | 2.77 | 16.8 | 16.67 | >5.56 | - |
1d | 26.50 | 11.84 | 2.2 | 66.10 | 1.69 | 39.1 | NT | NT | NT | 28.87 | >16.67 | - |
2a | 64.04 | >10.60 | - | 55.13 | 3.52 | 15.7 | 89.63 | 32.95 | 2.7 | 28.87 | >16.67 | - |
2b | 288.23 | 41.26 | 7.0 | 257.52 | 31.34 | 8.2 | >200 | >66.67 | <3.0 | 16.67 | >5.56 | - |
2c | 133.16 | 11.59 | 11.5 | 103.36 | 1.24 | 83.5 | 105.44 | 10.48 | 10.1 | 28.87 | >16.67 | - |
2d | 434.24 | 34.43 | 11.6 | 100.35 | 9.29 | 10.8 | 136.53 | >66.67 | <2.0 | NT | NT | NT |
2e | 87.30 | 10.95 | 8.0 | 29.08 | 3.55 | 8.2 | 45.78 | 17.72 | 2.6 | 19.25 | >11.11 | - |
2f | 425.44 | >98.32 | - | 295.10 | 56.73 | 5.2 | NT | NT | NT | NT | NT | NT |
2g | 56.04 | 9.04 | 6.2 | 80.80 | 8.98 | 9.0 | 27.57 | 14.18 | 1.9 | NT | NT | NT |
3a | 21.08 | >10.13 | - | 21.08 | 10.13 | 2.1 | 108.82 | 48.99 | 2.2 | 28.87 | >16.67 | - |
3b | 55.95 | 10.02 | 5.6 | 67.23 | 5.66 | 11.9 | 126.59 | 38.01 | 3.3 | 57.74 | >33.33 | - |
3c | 45.01 | 12.47 | 3.6 | 112.45 | 7.23 | 15.6 | NT | NT | NT | NT | NT | NT |
3d | 272.01 | 3.36 | 80.8 | 181.3 | 1.82 | 99.5 | 142.86 | 22.50 | 6.3 | 9.62 | >5.56 | - |
3e | 24.10 | 8.60 | 2.8 | 20.05 | 1.16 | 17.2 | 43.58 | 9.75 | 4.5 | 9.62 | >5.56 | - |
3f | 21.66 | 4.15 | 5.2 | 12.48 | 3.21 | 3.9 | 54.99 | 5.04 | 10.9 | 28.87 | 5.06 | 5.7 |
3g | 94.60 | 26.24 | 3.6 | 65.57 | 5.03 | 13.0 | 138.38 | 34.87 | 4.5 | 21.48 | 0.71 | 30.3 |
3h | 78.14 | 6.58 | 11.9 | 65.03 | 10.43 | 6.2 | 153.72 | 47.64 | 3.2 | NT | NT | NT |
3i | 27.42 | 3.42 | 8.0 | 13.18 | 2.53 | 5.2 | 38.24 | 9.81 | 3.9 | 9.62 | >5.56 | - |
3j | 826.44 | 213.80 | 3.9 | 826.44 | 52.98 | 15.6 | >200 | >66.67 | <3.0 | 28.87 | >16.67 | - |
3k | 1.73 | >0.41 | - | 2.09 | - | - | NT | NT | NT | NT | NT | NT |
4a | 14.84 | 4.93 | 3.0 | 25.75 | 6.38 | 4.0 | 79.04 | 5.51 | 14.3 | NT | NT | NT |
4b | 440.02 | 21.43 | 20.5 | 254.07 | 48.89 | 5.2 | >200 | 24.37 | >8.2 | >50 | >50 | - |
RBV | 4765.44 | 8.76 | 544.0 | 8205.90 | 2120.4 | 3.9 | NT | NT | NT | NT | NT | NT |
Oseltamivir | 4030.42 | 18.97 | 212.5 | NT | NT | NT | NT | NT | NT | NT | NT | NT |
3TC | NT | NT | NT | NT | NT | NT | NT | NT | NT | >100 | 1.85 | >54.1 |
Telaprevir | NT | NT | NT | NT | NT | NT | 32.12 | 0.011 | 2920.0 | NT | NT | NT |
2.2.2. Anti Cox B3 Virus Activity
2.2.3. Anti HCV Activity
2.2.4. Anti-HBV Activity
3. Experimental
3.1. General Information
3.2. Chemistry
3.2.1. General procedure for the synthesis of 1M–4M
3.2.2. General procedure for the synthesis of 1a–1e, 2a–2g, 3a–3f
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Zhang, D.-J.; Sun, W.-F.; Zhong, Z.-J.; Gao, R.-M.; Yi, H.; Li, Y.-H.; Peng, Z.-G.; Li, Z.-R. Synthesis and Broad-Spectrum Antiviral Activity of Some Novel Benzo-Heterocyclic Amine Compounds. Molecules 2014, 19, 925-939. https://doi.org/10.3390/molecules19010925
Zhang D-J, Sun W-F, Zhong Z-J, Gao R-M, Yi H, Li Y-H, Peng Z-G, Li Z-R. Synthesis and Broad-Spectrum Antiviral Activity of Some Novel Benzo-Heterocyclic Amine Compounds. Molecules. 2014; 19(1):925-939. https://doi.org/10.3390/molecules19010925
Chicago/Turabian StyleZhang, Da-Jun, Wen-Fang Sun, Zhao-Jin Zhong, Rong-Mei Gao, Hong Yi, Yu-Huan Li, Zong-Gen Peng, and Zhuo-Rong Li. 2014. "Synthesis and Broad-Spectrum Antiviral Activity of Some Novel Benzo-Heterocyclic Amine Compounds" Molecules 19, no. 1: 925-939. https://doi.org/10.3390/molecules19010925