Abstract
An efficient synthesis involving a key aldol reaction and biological properties of 1,3-diphenyl-2-propen-1-ones 8- 20 is described. The in vitro activity for 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging of 10 and 11 was 2 times higher than that for resveratrol. Compounds 9 and 11 were the strongest in suppression of in vitro nitric oxide (NO) generation and antiexcitotoxicity. Molecular modeling proposes an electron-donating group at the para position of acetophenones that leads to a dramatic increase in the suppression of NO production.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry
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Animals
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Cell Line
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Cell Survival / drug effects
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Chalcone / chemical synthesis*
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Chalcone / chemistry
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Chalcone / pharmacology*
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Glutarates / pharmacology
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Lipopolysaccharides / pharmacology
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Mice
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Models, Molecular
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Molecular Structure
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Neurons / drug effects
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Neurons / metabolism
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Neuroprotective Agents / chemical synthesis*
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Neuroprotective Agents / chemistry
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Neuroprotective Agents / pharmacology*
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Nitric Oxide / biosynthesis
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Structure-Activity Relationship
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Tissue Culture Techniques
Substances
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Aldehydes
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Glutarates
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Lipopolysaccharides
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Neuroprotective Agents
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glutaconic acid
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Nitric Oxide
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Chalcone
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3-hydroxybutanal