Synthesis, Characterization and Activity Evaluation of Matrinic Acid Derivatives as Potential Antiproliferative Agents
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Antiproliferative Activity
Compound | ClogP a | IC50 (μg/mL) | |||
---|---|---|---|---|---|
A375 | A549 | HeLa | HepG2 | ||
Matrine | 1.5 | 551.1 ± 22 | 1022.0 ± 16.5 | 1238.0 ± 5.7 | 1156.5 ± 11.9 |
2 | −0.704 | 1345.7 ± 125.6 | NA b | NA b | NA b |
4 | 1.572 | 853.1 ± 4.2 | NA b | 2201.5 ± 3.5 | 734.9 ± 24.4 |
5a | 4.218 | 138.7 ± 12.8 | 235.5 ± 1.6 | 223.5 ± 4.9 | 447.9 ± 34.4 |
5b | 4.747 | 116.7 ± 17 | 37.9 ± 2.3 | 121.2 ± 4.8 | 176.3 ± 5.6 |
5c | 5.276 | 60.7 ± 1.2 | 36.2 ± 1.3 | 118.8 ± 9.3 | 128.4 ± 2.3 |
5d | 5.056 | 58.5 ± 0.1 | 45.9 ± 0.1 | 102.9 ± 1.4 | 138.9 ± 9.2 |
5e | 5.805 | 37.0 ± 0.2 | 64.3 ± 6.2 | 75.5 ± 5.0 | 78.9 ± 0.4 |
5f | 3.796 | 82.8 ± 17.2 | 80.8 ± 2.7 | 758.2 ± 16.4 | 1383.3 ± 72.2 |
5g | 3.233 | 252 ± 1.4 | 47.0 ± 8.2 | 297.0 ± 27.6 | 143.6 ± 8.2 |
5h | 3.458 | 70.8 ± 7.0 | 41.5 ± 1.5 | 223.5 ± 4.9 | 100.9 ± 6.9 |
5i | 3.958 | 59.3 ± 0.9 | 70.6 ± 8.6 | 89.2 ± 0.6 | 61.0 ± 1.4 |
Taxol | — | 31.3 ± 1.0 | 39.4 ± 0.9 | 18.3 ± 3.1 | 85.1 ± 6.2 |
3. Experimental
3.1. General
3.2. General Procedure for the Preparation of Matrinic Acid 2
3.3. General Procedure for the Preparation of 3
3.4. General Procedure for the Preparation of 4
3.5. General Procedure for the Preparation of 5a–e
3.6. General Procedure for the Preparation of 5f–i
3.7. Antiproliferative Studies
4. Conclusions
Supplementary Materials
Acknowledgments
Conflicts of Interest
References
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Chao, F.; Wang, D.-E.; Liu, R.; Tu, Q.; Liu, J.-J.; Wang, J. Synthesis, Characterization and Activity Evaluation of Matrinic Acid Derivatives as Potential Antiproliferative Agents. Molecules 2013, 18, 5420-5433. https://doi.org/10.3390/molecules18055420
Chao F, Wang D-E, Liu R, Tu Q, Liu J-J, Wang J. Synthesis, Characterization and Activity Evaluation of Matrinic Acid Derivatives as Potential Antiproliferative Agents. Molecules. 2013; 18(5):5420-5433. https://doi.org/10.3390/molecules18055420
Chicago/Turabian StyleChao, Fan, Dong-En Wang, Rui Liu, Qin Tu, Jian-Jun Liu, and Jinyi Wang. 2013. "Synthesis, Characterization and Activity Evaluation of Matrinic Acid Derivatives as Potential Antiproliferative Agents" Molecules 18, no. 5: 5420-5433. https://doi.org/10.3390/molecules18055420