Synthesis and Antitumor Evaluation of 6-Aryl-substituted benzo[j]phenanthridine- and Benzo[g]pyrimido[4,5-c]isoquinolinequinones
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Cytotoxic Activities
3. Experimental
3.1. General
3.2. Anticancer Assay
4. Conclusions
Acknowledgments
References
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Sample Availability: Samples of compounds 7a,7b,7d, 8a–f are available from the authors. |
Acylnaphthohydroquinone | Enaminone | Product | N° | Yield (%) |
---|---|---|---|---|
4a | 5 | 7a | 45 | |
4b | 5 | 7b | 93 | |
4c | 5 | 7c | 26 | |
4d | 5 | 7d | 95 | |
4e | 5 | 7e | 16 | |
4f | 5 | 7f | 11 | |
4a | 6 | 8a | 81 | |
4b | 6 | 8b | 68 | |
4c | 6 | 8c | 73 | |
4d | 6 | 8d | 81 | |
4e | 6 | 8e | 25 | |
4f | 6 | 8f | 39 |
IC50 ± SEM a (µM) | |||||
---|---|---|---|---|---|
Compound | N° | MRC-5 b | AGS c | SK-MES-1 d | J82 e |
1 | 41.3 ± 2.2 | 19.0 ± 0.9 | 51.6 ± 2.7 | 62.6 ± 3.4 | |
7a | 35.4 ± 2.8 | 21.4 ± 1.3 | >100 | 99.4 ± 6.6 | |
7c | >100 | 42.4 ± 2.3 | >100 | >100 | |
7d | 14.3 ± 1.2 | 40.5 ± 2.6 | 64.4 ± 3.2 | 59.7 ± 2.5 | |
7e | 32.3 ± 2.6 | 47.8 ± 2.5 | >100 | >100 | |
7f | 21.3 ± 1.1 | 10.1 ± 0.8 | >100 | >100 | |
2 | 72.8 ± 3.4 | 82.1± 4.4 | 67.5 ± 3.6 | 78.6 ± 3.9 | |
8a | 30.3 ± 3.1 | 4.6 ± 0.2 | 12.4 ± 1.2 | 5.0 ± 0.3 | |
8b | 61.1 ± 5.4 | 36.1 ± 2.0 | 85.8 ± 5.1 | >100 | |
8c | 31.8 ± 2.5 | 3.3 ± 0.2 | >100 | >100 | |
8d | >100 | 19.6 ± 1.4 | >100 | 40.3 ± 3.3 | |
8e | 59.1 ± 4.6 | 18.5 ± 1.3 | 59.8 ± 4.5 | 23.4 ± 1.1 | |
8f | 77.8 ± 5.3 | >100 | 74.1 ± 5.8 | >100 | |
etoposide | - | 3.9 ± 0.21 | 0.36 ± 0.15 | 2.8 ± 0.18 | 0.80 ± 0.04 |
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Iribarra, J.; Vásquez, D.; Theoduloz, C.; Benites, J.; Ríos, D.; Valderrama, J.A. Synthesis and Antitumor Evaluation of 6-Aryl-substituted benzo[j]phenanthridine- and Benzo[g]pyrimido[4,5-c]isoquinolinequinones. Molecules 2012, 17, 11616-11629. https://doi.org/10.3390/molecules171011616
Iribarra J, Vásquez D, Theoduloz C, Benites J, Ríos D, Valderrama JA. Synthesis and Antitumor Evaluation of 6-Aryl-substituted benzo[j]phenanthridine- and Benzo[g]pyrimido[4,5-c]isoquinolinequinones. Molecules. 2012; 17(10):11616-11629. https://doi.org/10.3390/molecules171011616
Chicago/Turabian StyleIribarra, Jennyfer, David Vásquez, Cristina Theoduloz, Julio Benites, David Ríos, and Jaime A. Valderrama. 2012. "Synthesis and Antitumor Evaluation of 6-Aryl-substituted benzo[j]phenanthridine- and Benzo[g]pyrimido[4,5-c]isoquinolinequinones" Molecules 17, no. 10: 11616-11629. https://doi.org/10.3390/molecules171011616