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Practical Synthesis of Chalcone Derivatives and Their Biological Activities
- Practical Synthesis of Chalcone Derivatives and Their Biological Activities
- Jung, Jae-Chul; Lee, Yongnam; Min, Dongguk; Jung, Mankil; Oh, Seikwan
- Ewha Authors
- 오세관; 정재철
- SCOPUS Author ID
- Issue Date
- Journal Title
- vol. 22, no. 11
- condensation reaction; free radical scavenging; NO generation; neurotoxicity; molecular modelling; chalcones
- MDPI AG
- SCIE; SCOPUS
- Practical 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 mu M and especially compound 8 showed very potent anti-inflammatory activity with 1 mu M. 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.
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