Synthesis and Biological Evaluation of 2,3,4-Triaryl-1,2,4-oxadiazol-5-ones as p38 MAPK Inhibitors
Abstract
:1. Introduction
2. Results and Discussion
2.1. Design
2.2. Synthesis of 2,4-Oxazolidinyl-5-Ones (Azastilbenes)
2.3. Inhibition of p38α MAPK for Compounds 3a–l
3. Experimental Section
3.1. Materials and Methods
3.2. General Procedure
3.3. p38 MAP Kinase Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Entry | R1 a | R2 a | Ar | Product (Yield%) |
---|---|---|---|---|
1 | Ph | Py | 4-NO2-C6H4 | 3a (76%) |
2 | Ph | Py | 4-F-C6H4 | 3b (77%) |
3 | Ph | Py | 4-CF3-C6H4 | 3c (75%) |
4 | Ph | Py | 4-Cl-C6H4 | 3d (78%) |
5 | PhCH2 | Py | 4-F-C6H4 | 3e (62%) |
6 | PhCH2 | Py | 4-NO2-C6H4 | 3f (58%) |
7 | PhCH2 | Ph | 4-F-C6H4 | 3g (60%) |
8 | PhCH2 | Ph | 4-NO2-C6H4 | 3h (55%) |
9 | PhCH2 | Me | 4-F-C6H4 | 3i (75%) |
10 | Ph | Me | 4-F-C6H4 | 3l (78%) |
Entry | Compound | R1 | R2 | Ar | IC50-Value (μM) a |
---|---|---|---|---|---|
1 | 3a | Ph | Py | 4-NO2-C6H4 | 2.1 |
2 | 3b | Ph | Py | 4-F-C6H4 | 0.1 |
3 | 3c | Ph | Py | 4-CF3-C6H4 | 2.0 |
4 | 3d | Ph | Py | 4-Cl-C6H4 | 1.5 |
5 | 3e | PhCH2 | Py | 4-F-C6H4 | 0.08 |
6 | 3f | PhCH2 | Py | 4-NO2-C6H4 | 0.15 |
7 | 3g | PhCH2 | Ph | 4-F-C6H4 | 15.1 |
8 | 3h | PhCH2 | Ph | 4-NO2-C6H4 | 60.5 |
9 | 3i | PhCH2 | Me | 4-F-C6H4 | 18.5 |
10 | 3l | Ph | Me | 4-F-C6H4 | 22.8 |
SB 203580 | 0.3 |
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Romeo, R.; Giofrè, S.V.; Chiacchio, M.A.; Veltri, L.; Celesti, C.; Iannazzo, D. Synthesis and Biological Evaluation of 2,3,4-Triaryl-1,2,4-oxadiazol-5-ones as p38 MAPK Inhibitors. Molecules 2021, 26, 1745. https://doi.org/10.3390/molecules26061745
Romeo R, Giofrè SV, Chiacchio MA, Veltri L, Celesti C, Iannazzo D. Synthesis and Biological Evaluation of 2,3,4-Triaryl-1,2,4-oxadiazol-5-ones as p38 MAPK Inhibitors. Molecules. 2021; 26(6):1745. https://doi.org/10.3390/molecules26061745
Chicago/Turabian StyleRomeo, Roberto, Salvatore V. Giofrè, Maria A. Chiacchio, Lucia Veltri, Consuelo Celesti, and Daniela Iannazzo. 2021. "Synthesis and Biological Evaluation of 2,3,4-Triaryl-1,2,4-oxadiazol-5-ones as p38 MAPK Inhibitors" Molecules 26, no. 6: 1745. https://doi.org/10.3390/molecules26061745