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Practical Synthesis of Chalcone Derivatives and Their Biological Activities

Title
Practical Synthesis of Chalcone Derivatives and Their Biological Activities
Authors
Jung, Jae-ChulLee, YongnamMin, DonggukJung, MankilOh, Seikwan
Ewha Authors
오세관정재철
SCOPUS Author ID
오세관scopus
Issue Date
2017
Journal Title
MOLECULES
ISSN
1420-3049JCR Link
Citation
vol. 22, no. 11
Keywords
chalconescondensation reactionfree radical scavengingNO generationneurotoxicitymolecular modelling
Publisher
MDPI AG
Indexed
SCIE; SCOPUS WOS scopus
Abstract
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.
DOI
10.3390/molecules22111872
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의과대학 > 의학과 > Journal papers
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