Enantiopure Indolo[2,3-a]quinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biological Activity
3. Materials and Methods
3.1. General Information
3.2. Synthesis of (R)-Tryptophanol
3.3. General Procedure for the Synthesis of Compounds 6a–b, and 15
3.4. General Procedure for the Synthesis of Compounds 10 and 12
3.5. General Procedure for the Synthesis of Compounds 7a–c, 8a–b, 11, 13 and 16
3.6. Synthesis of (1R,6S,12bR)-1-Ethyl-6-(methoxymethyl)-12-methyl-1,2,3,6,7,12b-hexahydroindolo [2,3-a]quinolizin-4(12H)-one (14)
3.7. NMDA Receptor Antagonist Activity
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Compound | NMDA (100 μM) |
---|---|
IC50 μM a | |
4 | 63.4 ± 9.0 |
7a | 30.4 ± 2.5 |
Amantadine | 88.5 ± 11.8 |
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Pereira, N.A.L.; Sureda, F.X.; Pérez, M.; Amat, M.; Santos, M.M.M. Enantiopure Indolo[2,3-a]quinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists. Molecules 2016, 21, 1027. https://doi.org/10.3390/molecules21081027
Pereira NAL, Sureda FX, Pérez M, Amat M, Santos MMM. Enantiopure Indolo[2,3-a]quinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists. Molecules. 2016; 21(8):1027. https://doi.org/10.3390/molecules21081027
Chicago/Turabian StylePereira, Nuno A. L., Francesc X. Sureda, Maria Pérez, Mercedes Amat, and Maria M. M. Santos. 2016. "Enantiopure Indolo[2,3-a]quinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists" Molecules 21, no. 8: 1027. https://doi.org/10.3390/molecules21081027