Efficient synthesis and neuroprotective effect of substituted 1,3-diphenyl-2-propen-1-ones.
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.
Jung
Jae-Chul
JC
Department of Neuroscience and Medical Research Institute, School of Medicine, Ewha Womans University, Seoul 158-710, Korea.
Jang
Soyong
S
Lee
Yongnam
Y
Min
Dongguk
D
Lim
Eunyoung
E
Jung
Heyin
H
Oh
Miyeon
M
Oh
Seikwan
S
Jung
Mankil
M
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D002599:Chalcone / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005977:Glutarates / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure; D009474:Neurons / Q000187:drug effects / Q000378:metabolism; D018696:Neuroprotective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009569:Nitric Oxide / Q000096:biosynthesis; D013329:Structure-Activity Relationship; D046509:Tissue Culture Techniques
D000447:Aldehydes; D005977:Glutarates; D008070:Lipopolysaccharides; D018696:Neuroprotective Agents; C010971:glutaconic acid; D009569:Nitric Oxide; D002599:Chalcone; C116609:3-hydroxybutanal