Design, Synthesis and Biological Evaluation of 1,4-Disubstituted-3,4-dihydroisoquinoline Compounds as New Tubulin Polymerization Inhibitors
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
Compound | R1 | R2 | IC50 (μM) |
---|---|---|---|
CEM | |||
20 | 3',4'-OCH3 | 36.29 | |
21 | 3'-NH2-4'-OCH3 | 4.10 | |
22 | 3'-NHCOCH3-4'-OCH3 | 24.32 | |
23 | 4'-OCH3 | 17.76 | |
24 | 4'-OH | 40.33 | |
25 | 4'-OCOCH3 | >100 | |
26 | 4'-F | 44.58 | |
27 | 4'-CH3 | >100 | |
28 | 3'-CH3 | 44.07 | |
29 | 3'-NH2-4'-OCH3 | 46.11 | |
30 | 4'-OH | 32.48 | |
31 | 2',4'-F | 3.08 | |
32 | 2',4'-F | 0.64 | |
2a | 3'-NO2-4'-OCH3 | 29.25 | |
2b | 2',4'-F | 15.21 | |
Colchicine | / | / | 0.004 |
2.2. In Vitro Cytotoxic Activity
2.3. In Vitro Tubulin Polymerization Inhibitory Activity
2.4. Molecular Docking Study
3. Experimental Section
3.1. Chemistry
3.2. In Vitro Cytotoxic Activity
3.3. In Vitro Tubulin Polymerization Inhibitory Activity
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Zhang, L.; Song, Y.; Huang, J.; Liu, J.; Zhu, W.; Zhou, Y.; Lv, J.; Zheng, C.; Zhu, J. Design, Synthesis and Biological Evaluation of 1,4-Disubstituted-3,4-dihydroisoquinoline Compounds as New Tubulin Polymerization Inhibitors. Int. J. Mol. Sci. 2015, 16, 10173-10184. https://0-doi-org.brum.beds.ac.uk/10.3390/ijms160510173
Zhang L, Song Y, Huang J, Liu J, Zhu W, Zhou Y, Lv J, Zheng C, Zhu J. Design, Synthesis and Biological Evaluation of 1,4-Disubstituted-3,4-dihydroisoquinoline Compounds as New Tubulin Polymerization Inhibitors. International Journal of Molecular Sciences. 2015; 16(5):10173-10184. https://0-doi-org.brum.beds.ac.uk/10.3390/ijms160510173
Chicago/Turabian StyleZhang, Ling, Yunlong Song, Jingjing Huang, Jia Liu, Wenwen Zhu, Youjun Zhou, Jiaguo Lv, Canhui Zheng, and Ju Zhu. 2015. "Design, Synthesis and Biological Evaluation of 1,4-Disubstituted-3,4-dihydroisoquinoline Compounds as New Tubulin Polymerization Inhibitors" International Journal of Molecular Sciences 16, no. 5: 10173-10184. https://0-doi-org.brum.beds.ac.uk/10.3390/ijms160510173