Synthesis, Characterization, and Anti-Inflammatory Activities of Methyl Salicylate Derivatives Bearing Piperazine Moiety
Abstract
:1. Introduction
2. Results
2.1. Synthesis of Salicylate Derivatives Bearing Piperazine Moiety
2.2. In Vivo Anti-Inflammatory Activities of Salicylate Derivatives Bearing Piperazine Moiety
2.3. Cytotoxicity Assays of Compounds M2, M14, M15, and M16
2.4. Inhibitory Screening against Lipopolysaccharide (LPS)-Induced Interleukin (IL)-6 and Tumor Necrosis Factor (TNF)-α Release
2.5. Compound M16 Attenuates LPS Induced Cyclooxygenase-2 (COX-2) Up-Regulation
3. Experimental Section
3.1. Synthetic Details of Intermediates and Target Compounds
3.2. Cell Culture and Cytotoxicity Assays
3.3. In Vivo Anti-Inflammatory Activity Assays in Ear and Paw Edema
3.4. ELISA Assay
3.5. Western Blot Assays
3.6. Statistical Analysis
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Compound | Dose (mg/kg) | Ear Edema | Paw Edema | Dose (mmol/kg) | ||
---|---|---|---|---|---|---|
Swelling Degree (mg) | Inhibition (%) | Swelling Degree (mg) | Inhibition (%) | |||
Control | 8.36 ± 2.50 | - | 94.93 ± 8.46 | - | ||
M1 | 100 | 2.82 ± 0.56 *** | 66.25 | 59.31 ± 6.25 *** | 37.52 | 0.25 |
M2 | 100 | 2.29 ± 0.47 *** | 72.65 | 43.44 ± 8.65 *** | 54.24 | 0.23 |
M3 | 100 | 2.42 ± 0.44 *** | 71.09 | 50.58 ± 7.40 *** | 46.72 | 0.23 |
M4 | 100 | 2.70 ± 0.49 *** | 67.67 | 54.82 ± 5.03 ** | 42.25 | 0.24 |
M5 | 100 | 4.61 ± 1.11 ** | 44.82 | 57.98 ± 4.94 ** | 38.92 | 0.24 |
M6 | 100 | 4.54 ± 1.16 ** | 45.70 | 61.04 ± 5.58 *** | 35.70 | 0.23 |
M7 | 100 | 5.03 ± 1.77 * | 39.80 | 64.58 ± 6.75 *** | 31.97 | 0.23 |
M8 | 100 | 4.05 ± 1.55 ** | 51.55 | 59.60 ± 6.86 *** | 37.21 | 0.20 |
M9 | 100 | 4.63 ± 1.43 ** | 44.65 | 59.22 ± 5.21 *** | 37.62 | 0.23 |
M10 | 100 | 4.07 ± 1.08 ** | 51.30 | 79.22 ± 7.06 ** | 16.55 | 0.23 |
M11 | 100 | 3.74 ± 1.13 *** | 55.31 | 49.24 ± 7.79 *** | 48.13 | 0.25 |
M12 | 100 | 4.31 ± 1.37 ** | 48.40 | 59.91 ± 7.72 *** | 36.89 | 0.24 |
M13 | 100 | 3.61 ± 1.17 *** | 56.80 | 53.43 ± 6.01 *** | 43.72 | 0.23 |
M14 | 100 | 2.43 ± 0.75 *** | 70.97 | 43.64 ± 6.37 *** | 54.03 | 0.32 |
M15 | 100 | 2.13 ± 1.09 *** | 74.48 | 41.42 ± 7.07 *** | 56.37 | 0.24 |
M16 | 100 | 1.53 ± 0.55 *** | 81.73 | 33.43 ± 6.92 *** | 64.78 | 0.20 |
Aspirin | 100 | 4.85 ± 1.70 * | 41.96 | 67.24 ± 8.68 *** | 29.16 | 0.56 |
Indomethacin | 5 | 4.96 ± 1.09 ** | 40.66 | 64.13 ± 8.91 *** | 32.45 | 0.01 |
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Li, J.; Yin, Y.; Wang, L.; Liang, P.; Li, M.; Liu, X.; Wu, L.; Yang, H. Synthesis, Characterization, and Anti-Inflammatory Activities of Methyl Salicylate Derivatives Bearing Piperazine Moiety. Molecules 2016, 21, 1544. https://doi.org/10.3390/molecules21111544
Li J, Yin Y, Wang L, Liang P, Li M, Liu X, Wu L, Yang H. Synthesis, Characterization, and Anti-Inflammatory Activities of Methyl Salicylate Derivatives Bearing Piperazine Moiety. Molecules. 2016; 21(11):1544. https://doi.org/10.3390/molecules21111544
Chicago/Turabian StyleLi, Jingfen, Yong Yin, Lisheng Wang, Pengyun Liang, Menghua Li, Xu Liu, Lichuan Wu, and Hua Yang. 2016. "Synthesis, Characterization, and Anti-Inflammatory Activities of Methyl Salicylate Derivatives Bearing Piperazine Moiety" Molecules 21, no. 11: 1544. https://doi.org/10.3390/molecules21111544