Abstract
Starting from dehydrobaietic acid with the analogous structure of carnosic acid, the intermediate methyl 12-bromo-13-nitro-7-oxo dehydrodeisopropylabietate was synthesized through methylation, bromination, carbonylation, and nitration. Subsequently, the coupling of methyl 12-bromo-13-nitro-7-oxo dehydrodeisopropylabietate with aliphatic or aromatic primary amine by Ullmann condensation reaction produced a series of methyl 12-imino-13-nitro-7-oxo dehydrodeisopropylabietate derivatives. In order to probe their antioxidant effects through metal ion chelation mechanism, the metal ion binding abilities on Cu2+ and Fe2+ of these compounds were studied using fluorescence quenching method. The results indicated that each compound showed obvious chelation activity with the binding constants (K A) of the 102 L mol−1 order of magnitude, which implied its potential pharmacology application as antioxidant by the inhibition of Feton reaction through chelation with Cu2+ and Fe2+.
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Acknowledgments
This study was supported by 973 projects (2011CB512005), Guangxi Natural Science Foundation of China (2011GXNSFD018010 and 2010GXNSFF013001), The projects of Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University) Ministry of Education of China (CMEMR2011-15), School of Chemistry & Chemical Engineering of, Guangxi’s Medicine Talented Persons Small Highland Foundation (0808), and The Scientific Research and Technological Development Project of Guilin (No. 20110106-2).
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Wang, K., Liu, X., Yi, X. et al. Synthesis and metal ion binding activity of methyl 12-amino-13-nitro-7-oxo dehydrodeisopropylabietate derivatives. Med Chem Res 21, 2494–2500 (2012). https://doi.org/10.1007/s00044-011-9766-2
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DOI: https://doi.org/10.1007/s00044-011-9766-2