Synthesis and Antiviral Activity of Novel 1,4-Pentadien-3-one Derivatives Containing a 1,3,4-Thiadiazole Moiety
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Antiviral Activity of Title Compounds against TMV In Vivo
2.3. Antiviral Activity of Title Compounds against CMV In Vivo
2.4. Antiviral Activity and Structure-Activity Relationships
3. Materials and Methods
3.1. General Information
3.2. Chemistry
3.2.1. General Procedure for Preparation of Intermediates 3a–3t
3.2.2. General Procedure for Preparation of Title Compounds 4a–4t
3.3. Antiviral Biological Assay
3.3.1. Purification of TMV and CMV
3.3.2. Curative Activities of Compounds against TMV and CMV In Vivo
3.3.3. Protective Activities of Compounds against TMV and CMV In Vivo
3.3.4. Inactivation Activities of Compounds aga inst TMV and CMV In Vivo
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 4a–4t are available from the authors. |
No. | Solvent | Base | Temperature (°C) | Yield (%) a |
---|---|---|---|---|
1 | DMF | Et3N | 25 | 0 |
2 | DMF | K2CO3 | 25 | 21 |
3 | DMF | K2CO3 | 50 | 38 |
4 | acetone | KOH | 25 | 18 |
5 | THF | KOH | 25 | 26 |
6 | CH3CN | KOH | 25 | 38 |
7 | DMF | KOH | 25 | 56 |
8 | DMF | KOH | 40 | 87 |
9 | DMF | NaOH | 40 | 72 |
Compound | Curative Activity (%) a | Protection Activity (%) a | Inactivation Activity (%) a | EC50 of Protection Activity (µg/mL) a |
---|---|---|---|---|
4a | 55.8 ± 3.1 | 55.9 ± 3.5 | 84.1 ± 4.8 | 344.23 ± 2.35 |
4b | 56.4 ± 1.5 | 64.5 ± 1.1 | 84.1 ± 4.8 | 319.67 ± 1.89 |
4c | 36.8 ± 0.6 | 52.2 ± 1.4 | 91.8 ± 3.8 | 411.42 ± 2.68 |
4d | 21.2 ± 1.5 | 24.2 ± 2.1 | 64.3 ± 2.6 | 1058.25 ± 2.11 |
4e | 45.0 ± 1.6 | 30.4 ± 2.1 | 82.4 ± 1.8 | 1042.09 ± 1.28 |
4f | 40.6 ± 0.8 | 61.6 ± 3.3 | 90.1 ± 0.3 | 389.46 ± 2.32 |
4g | 56.3 ± 2.7 | 46.3 ± 1.4 | 78.5 ± 1.9 | 592.44 ± 1.89 |
4h | 56.2 ± 3.5 | 70.2 ± 1.3 | 93.8 ± 1.7 | 105.01 ± 3.15 |
4i | 53.7 ± 1.6 | 64.3 ± 2.7 | 85.3 ± 2.0 | 254.77 ± 1.66 |
4j | 44.6 ± 3.2 | 53.6 ± 3.7 | 85.2 ± 2.2 | 388.31 ± 2.05 |
4k | 56.5 ± 2.1 | 68.4 ± 1.8 | 87.1 ± 3.6 | 135.38 ± 3.12 |
4l | 45.9 ± 3.1 | 63.4 ± 4.4 | 83.0 ± 1.9 | 297.40 ± 4.10 |
4m | 40.5 ± 1.8 | 54.8 ± 2.5 | 81.5 ± 1.2 | 334.03 ± 1.08 |
4n | 47.9 ± 2.5 | 59.8 ± 4.3 | 89.3 ± 2.5 | 309.09 ± 2.56 |
4o | 51.7 ± 2.8 | 64.8 ± 3.1 | 77.6 ± 1.3 | 248.18 ± 4.14 |
4p | 24.2 ± 4.5 | 50.7 ± 1.5 | 88.6 ± 1.1 | 466.15 ± 1.98 |
4q | 58.7 ± 3.0 | 68.4 ± 1.6 | 84.7 ± 2.6 | 129.87 ± 3.55 |
4r | 42.3 ± 2.4 | 56.7 ± 2.8 | 87.4 ± 2.9 | 316.77 ± 2.54 |
4s | 28.2 ± 3.8 | 59.0 ± 1.7 | 82.7 ± 1.6 | 316.52 ± 4.29 |
4t | 54.5 ± 4.4 | 54.1 ± 1.2 | 82.7 ± 1.6 | 425.71 ± 3.17 |
Ribavirin b | 37.9 ± 1.9 | 51.8 ± 2.3 | 72.9 ± 2.4 | 457.25± 2.68 |
Compound | Curative Activity (%) a | Protection Activity (%) a | Inactivation Activity (%) a |
---|---|---|---|
4a | 29.3 ± 1.3 | 40.1 ± 2.5 | 71.3 ± 3.1 |
4b | 23.6 ± 2.2 | 38.9 ± 2.9 | 65.2 ± 2.5 |
4c | 37.9 ± 3.7 | 43.4 ± 3.1 | 61.5 ± 2.2 |
4d | 18.5 ± 1.8 | 33.6 ± 2.1 | 51.2 ± 3.4 |
4e | 55.9 ± 1.8 | 42.3 ± 1.1 | 79.6 ± 4.2 |
4f | 50.2 ± 2.7 | 46.6 ± 2.3 | 62.5 ± 1.9 |
4g | 39.8 ± 2.5 | 48.5 ± 2.7 | 66.7 ± 2.2 |
4h | 39.8 ± 2.5 | 36.2 ± 2.2 | 62.1 ±1.9 |
4i | 37.3 ± 2.5 | 35.6 ± 2.1 | 51.8 ± 1.1 |
4j | 40.6 ± 3.7 | 45.9 ± 1.6 | 79.1± 2.5 |
4k | 26.4 ± 2.3 | 35.6 ± 1.9 | 49.9± 3.6 |
4l | 29.7 ± 1.1 | 43.5 ± 2.5 | 66.5 ± 2.0 |
4m | 28.5 ± 2.3 | 42.2 ± 1.4 | 68.9 ± 2.8 |
4n | 18.9 ± 2.9 | 25.4 ± 1.7 | 46.2 ± 0.9 |
4o | 31.8 ± 2.8 | 49.9 ± 1.9 | 58.2 ± 3.2 |
4p | 29.5 ± 1.4 | 38.5 ± 2.1 | 59.8 ± 1.9 |
4q | 44.5 ± 1.8 | 48.1 ± 2.4 | 43.9 ± 1.2 |
4r | 26.4 ± 2.2 | 40.5 ± 1.9 | 42.5 ± 2.8 |
4s | 41.0 ± 1.7 | 54.7 ± 2.4 | 78.5 ± 1.9 |
4t | 34.8 ± 2.3 | 48.1 ± 1.6 | 69.5 ± 2.0 |
Ribavirin b | 36.8 ± 1.6 | 47.9 ± 2.7 | 71.2 ± 1.7 |
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Yu, L.; Gan, X.; Zhou, D.; He, F.; Zeng, S.; Hu, D. Synthesis and Antiviral Activity of Novel 1,4-Pentadien-3-one Derivatives Containing a 1,3,4-Thiadiazole Moiety. Molecules 2017, 22, 658. https://doi.org/10.3390/molecules22040658
Yu L, Gan X, Zhou D, He F, Zeng S, Hu D. Synthesis and Antiviral Activity of Novel 1,4-Pentadien-3-one Derivatives Containing a 1,3,4-Thiadiazole Moiety. Molecules. 2017; 22(4):658. https://doi.org/10.3390/molecules22040658
Chicago/Turabian StyleYu, Lu, Xiuhai Gan, Dagui Zhou, Fangcheng He, Song Zeng, and Deyu Hu. 2017. "Synthesis and Antiviral Activity of Novel 1,4-Pentadien-3-one Derivatives Containing a 1,3,4-Thiadiazole Moiety" Molecules 22, no. 4: 658. https://doi.org/10.3390/molecules22040658
APA StyleYu, L., Gan, X., Zhou, D., He, F., Zeng, S., & Hu, D. (2017). Synthesis and Antiviral Activity of Novel 1,4-Pentadien-3-one Derivatives Containing a 1,3,4-Thiadiazole Moiety. Molecules, 22(4), 658. https://doi.org/10.3390/molecules22040658