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Molecules 2017, 22(11), 1872;

Practical Synthesis of Chalcone Derivatives and Their Biological Activities

Department of Molecular Medicine, School of Medicine, Ewha Womans University, Seoul 07985, Korea
Department of Chemistry, Yonsei University, Seoul 03722, Korea
Authors to whom correspondence should be addressed.
Received: 30 September 2017 / Revised: 21 October 2017 / Accepted: 24 October 2017 / Published: 1 November 2017
(This article belongs to the Special Issue Chalcone: A Privileged Structure in Medicinal Chemistry)
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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 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
Keywords: chalcones; condensation reaction; free radical scavenging; NO generation; neurotoxicity; molecular modelling chalcones; condensation reaction; free radical scavenging; NO generation; neurotoxicity; molecular modelling

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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.

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