Synthesis, Antiviral and Antifungal Bioactivity of 2-Cyano-acrylate Derivatives Containing Phosphonyl Moieties
Abstract
:Introduction
Results and Discussion
Entry | Solvent | Ratio a | Time (h) | Reaction temperature | Yield (%) b |
---|---|---|---|---|---|
1 | DMF | 1:3:3 | 16 | r.t | 11.2 |
2 | acetone | 1:3:3 | 16 | r.t | 19.0 |
3 | CH3CN | 1:3:3 | 16 | r.t | 34.9 |
4 | THF | 1:3:3 | 16 | r.t | 55.0 |
5 | THF | 1:3:1 | 16 | r.t | 12.0 |
6 | THF | 1:3:2 | 16 | r.t | 20.0 |
7 | THF | 1:1:1 | 16 | r.t | 0 |
8 | THF | 1:3:4 | 16 | r.t | 49.5 |
9 | THF | 1:3:3 | 4 | r.t | 0 |
10 | THF | 1:3:3 | 8 | r.t | 23.0 |
11 | THF | 1:3:3 | 20 | r.t | 56.0 |
12 | THF | 1:3:3 | 16 | 0-5°C | 23.0 |
13 | THF | 1:3:3 | 16 | 40-45°C | 13.0 |
Antifungal Bioassay: Inhibitory effects of cyanoacrylate derivatives on phytopathogenic fungi
Compd. | Conc. (μg/mL) | Inhibition rate (%) | ||||||
---|---|---|---|---|---|---|---|---|
Fusarium graminearum | Cytospora mandshurica | Fusarium oxysporum | ||||||
2a | 50 | 11.14±0.21 | 11.00±0.25 | 18.21±0.11 | ||||
500 | 37.30±0.56 | 24.00±0.77 | 26.03±0.99 | |||||
2b | 50 | 4.94±0.49 | 1.34±0.65 | 8.08±0.98 | ||||
500 | 31.40±0.78 | 35.03±0.84 | 36.83±1.24 | |||||
2c | 50 | 8.31±0.57 | 13.10±0.78 | 13.47±1.24 | ||||
500 | 37.10±1.08 | 31.82±1.45 | 41.02±1.30 | |||||
2d | 50 | 64.50±0.40 | 60.43±0.63 | 65.03±1.22 | ||||
500 | 93.30±4.28 | 90.59±1.59 | 92.75±2.52 | |||||
2e | 50 | 22.04±0.90 | 32.01±0.78 | 26.71±0.90 | ||||
500 | 41.44±1.21 | 36.77±1.45 | 32.13±1.09 | |||||
2f | 50 | 35.22±1.78 | 41.09±3.21 | 46.11±3.34 | ||||
500 | 55.64±3.01 | 66.09±2.55 | 68.9±1.19 | |||||
2g | 50 | 7.79±0.57 | -0.80±0.72 | 6.29±0.97 | ||||
500 | 40.0±2.15 | 49.47±1.01 | 48.80±1.33 | |||||
2h | 50 | 4.68±0.56 | -3.21±0.85 | 5.99±0.87 | ||||
500 | 25.41±0.73 | 23.26±0.84 | 36.53±1.27 | |||||
2i | 50 | 5.45±0.73 | -2.67±0.67 | 1.20±0.89 | ||||
500 | 16.3±0.64 | 8.29±0.76 | 20.06±0.97 | |||||
2j | 50 | 0.97±0.11 | 11.27±0.45 | 9.99±0.22 | ||||
500 | 20.00±0.21 | 26.78±0.44 | 30.99±1.09 | |||||
2k | 50 | 10.09±0.76 | 32.20±0.55 | 19.39±0.44 | ||||
500 | 31.03±0.90 | 36.38±1.32 | 40.22±1.45 | |||||
2l | 50 | 21.08±0.98 | 30.07±0.67 | 12.11±1.02 | ||||
500 | 34.01±1.67 | 29.51±1.02 | 32.00±0.69 | |||||
2m | 50 | 3.93±0.22 | 14.23±0.51 | 23.09±0.88 | ||||
500 | 27.31±0.99 | 16.08±0.55 | 41.90±2.01 | |||||
2n | 50 | 12.22±1.01 | 9.97±0.88 | 11.91±0.42 | ||||
500 | 24.04±0.62 | 36.09±0.55 | 35.69±1.90 | |||||
2o | 50 | 3.75±0.52 | 10.61±0.69 | 4.01±0.55 | ||||
500 | 21.08±0.65 | 48.28±0.96 | 29.07±0.65 | |||||
2p | 50 | 4.45±0.55 | 24.93±0.76 | 6.52±0.56 | ||||
500 | 28.10±0.69 | 47.21±0.95 | 35.59±0.69 | |||||
2q | 50 | 7.03±0.60 | 15.38±0.61 | 3.26±0.44 | ||||
500 | 42.15±0.79 | 57.82±1.11 | 33.58±0.68 | |||||
2r | 50 | 11.71±0.96 | 23.87±0.75 | 9.52±0.57 | ||||
500 | 44.03±0.81 | 64.72±1.26 | 52.13±0.84 | |||||
2s | 50 | 9.84±0.61 | 35.01±0.72 | 13.53±0.48 | ||||
500 | 53.40±0.92 | 65.78±1.29 | 56.64±0.90 | |||||
2t | 50 | 49.67±0.65 | 51.30±0.70 | 41.05±0.51 | ||||
500 | 81.97±2.91 | 75.33±1.71 | 69.42±1.23 | |||||
Hymexazol a | 50 | 73.2±1.41 | 58.89±1.16 | 65.51±1.76 | ||||
500 | 100±0.66 | 95.33±1.87 | 93.18±3.76 | |||||
DMSO b | 0 | 0 | 0 |
Micro-observation results
Conclusions
Experimental
General
General procedure for the preparation of title compounds 2a-2t.
Yields and product characterization
Antifungal bioassay
Hyphal morphology of F. oxysporum
Acknowledgments
References
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Lv, Y.-P.; Wang, X.-Y.; Song, B.-A.; Yang, S.; Yan, K.; Xu, G.-F.; Bhadury, P.S.; Liu, F.; Jin, L.-H.; Hu, D.-Y. Synthesis, Antiviral and Antifungal Bioactivity of 2-Cyano-acrylate Derivatives Containing Phosphonyl Moieties. Molecules 2007, 12, 965-978. https://doi.org/10.3390/12050965
Lv Y-P, Wang X-Y, Song B-A, Yang S, Yan K, Xu G-F, Bhadury PS, Liu F, Jin L-H, Hu D-Y. Synthesis, Antiviral and Antifungal Bioactivity of 2-Cyano-acrylate Derivatives Containing Phosphonyl Moieties. Molecules. 2007; 12(5):965-978. https://doi.org/10.3390/12050965
Chicago/Turabian StyleLv, Yin-Pu, Xian-You Wang, Bao-An Song, Song Yang, Kai Yan, Guang-Fang Xu, Pinaki S Bhadury, Fang Liu, Lin-Hong Jin, and De-Yu Hu. 2007. "Synthesis, Antiviral and Antifungal Bioactivity of 2-Cyano-acrylate Derivatives Containing Phosphonyl Moieties" Molecules 12, no. 5: 965-978. https://doi.org/10.3390/12050965