TY - JOUR
T1 - Practical synthesis of chalcone derivatives and their biological activities
AU - Jung, Jae Chul
AU - Lee, Yongnam
AU - Min, Dongguk
AU - Jung, Mankil
AU - Oh, Seikwan
N1 - Publisher Copyright:
© 2017 by the authors.
PY - 2017/11
Y1 - 2017/11
N2 - 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 M and especially compound 8 showed very potent anti-inflammatory activity with 1 M. In addition, the di- A nd 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.
AB - 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 M and especially compound 8 showed very potent anti-inflammatory activity with 1 M. In addition, the di- A nd 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.
KW - Chalcones
KW - Condensation Reaction
KW - Free Radical Scavenging
KW - Molecular modelling
KW - Neurotoxicity
KW - No Generation
UR - http://www.scopus.com/inward/record.url?scp=85033774243&partnerID=8YFLogxK
U2 - 10.3390/molecules22111872
DO - 10.3390/molecules22111872
M3 - Article
C2 - 29104222
AN - SCOPUS:85033774243
SN - 1420-3049
VL - 22
JO - Molecules
JF - Molecules
IS - 11
M1 - 1872
ER -