Practical Synthesis of Chalcone Derivatives and Their Biological Activities
AbstractPractical synthesis and biological activities of 4-hydroxy-3-methoxy-2-propene derivatives are described. The novel chalcone derivatives were prepared by acid catalysed one-step condensation of 1,3- or 1,4-diacetylbenzene and 1,3,5-triacetylbenzene with 4-hydroxy-3-methoxybenzaldehyde. They were then evaluated for free radical scavenging activity, suppression of lipopolysaccharides (LPS)-induced NO generation, and anti-excitotoxicity in vitro. It was found that all compounds showed good effects for 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging, LPS-induced NO generation, and anti-neurotoxicity. Compounds 6 and 7 were potent suppressor of NO generation with the concentration range 10 µM and especially compound 8 showed very potent anti-inflammatory activity with 1 µM. In addition, the di- and tri-acetylbenzyl derivatives 6, 7, and 8 showed enhanced anti-neurotoxicity activity in cultured cortical neurons. Molecular modelling studies to investigate the chemical structural characteristics required for the enhanced biological activities interestingly revealed that compound 8 has the smallest highest occupied molecular orbital-lowest energy unoccupied molecular orbital (HOMO-LUMO) gap, which signifies easy electron and radical transfer between HOMO and LUMO in model studies. View Full-Text
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Jung, J.-C.; Lee, Y.; Min, D.; Jung, M.; Oh, S. Practical Synthesis of Chalcone Derivatives and Their Biological Activities. Molecules 2017, 22, 1872.
Jung J-C, Lee Y, Min D, Jung M, Oh S. Practical Synthesis of Chalcone Derivatives and Their Biological Activities. Molecules. 2017; 22(11):1872.Chicago/Turabian Style
Jung, Jae-Chul; Lee, Yongnam; Min, Dongguk; Jung, Mankil; Oh, Seikwan. 2017. "Practical Synthesis of Chalcone Derivatives and Their Biological Activities." Molecules 22, no. 11: 1872.
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