• YAKHAK HOEJI
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• v.52 no.1
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• pp.62-66
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• 2008

In this study, we examined the inhibitory effects of propenone derivatives, 1,3-diphenyl-propenone (DPhP), 3-phenyl-1-thiophen-2-yl-propenone (PhT2P), 3-phenyl-1-thiophen-3-yl-propenone (PhT3P) and 1-furan-2-yl-3-phenyl-propenone (FPhP), on $TNF-{\alpha}$-induced nuclear factor (NF)-${\kappa}B$ activity and interleukin (IL)-8-induced monocyte adhesion to colon epithelial cells. 1-Furan-2-yl-3-pyridin-2-yl-propenone (FPP-3) that is previously reported as a $NF-{\kappa}B$ inhibitor suppressed $TNF-{\alpha}$-induced monocyte-epithelial cell adhesion in a concentration-dependent manner. The propenone derivatives, DPhP, PhT2P, PhT3P, FPhP, also inhibited $TNF-{\alpha}$-induced $NF-{\kappa}B$ activation in a similar degree to FPP-3. In a DPPH radical scavenging assay, none of the compounds showed DPPH radical scavenging activity, indicating that the inhibitory actions of the propenone derivatives on redox-sensitive $NF-{\kappa}B$ activity is not due to a simple free radical scavenging activity. In addition, the propenone derivatives also suppressed the IL-8-induced monocyte adhesion to colon epithelial cells. Furthermore, the effective concentrations of the propenone derivatives on both $NF-{\kappa}B$ activation as well as IL-8 induced monocyte-epithelial cell adhesion were 1000 times lower than 5-aminosalicylic acid (5-ASA), a clinically used drug for inflammatory bowel disease. These results suggest that the propenone derivatives may be a potential lead having a strong inhibitory activity against inflammatory cytokine-induced epithelial inflammation.

• Applied Biological Chemistry
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• v.37 no.4
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• pp.287-294
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• 1994

New 3-phenyl-1-(2-furyl)propenones, 1 and 3-phenyl-1-(2-furyl)-3-thiophenyl-propanone, 2 derivatives were synthesized, and their fungicidal activities in vitro against Botrytis cineria (BC), Valsa ceratosperma (VC), Scelerotium cepivorum (SC) and Phytophthora capsici (PC) were investigated using a generalized structure-activity relationship (SAR). The activity of 1 was superior to those of 2, and nonsubstituent, 1a and chloro group substituent, 1d of E (Syn) conformer were the most effective $(EC_{50}=10{\sim}12\;ppm)$ compound to BC. Antifungal activities were able to predict to depend essentially on the ${\beta}$ carbon and their positive charge from the results that the good correlation $(r^2=0.90)$ was observed between hydrolysis rate constant (logk) of 1 and the electronic parameter $({\sigma})$ of X-substituent on the ${\beta}-phenyl$ ring.

• Applied Biological Chemistry
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• v.46 no.4
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• pp.361-366
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• 2003

Anti-aflatoxigenic studies on synthetic pyridione alkaloids were conducted. Seven derivatives using piperlongumine as a leading compound were prepared from 3,4,5-trimethoxycinnamic acid (TMCA). These derivatives were analyzed for their structural confrmation and purity by HPLC, GC, GC/MS and $1^H-NMR$. 1-piperidin-1-yl-3-(3,4,5-trimethoxyphenyl)propenone (1) reaction with piperidine; 1-morpholin-4-yl-3-(3,4,5-trimethoypenyl)propenone (2) with morpholine; 1-(3,5-dimethylpiperidin-1-yl)-3-(3,4,5-trimethoxyphenyl)propenone (3) with 3,5-dimethylpiperdine; 1-(2-methylpiperidine-1-yl)-3-(3,4,5-trimethoxyphenyl)propenone (4) with 2-methylpiperidine; 1-(3-hydroxypiperidin-1-yl)-3- (3,4,5-trimethoxyphenyl)propenone (5) with 3-hydroxypiperidine hydrochloride; 1-[3- (3,4,5-trimethoxyphenyl)acryloyl]piperidin-2-one (6) with ${\delta}-valerolactam;\; and\;ethyl\;1-[3-(3,4,5-trimethoxyphenyl)acyloyl]piperidine-4-carboxylate$ (7) with ethyl isonipectotate were synthesized respectively. All derivatives showed an inhibitory activity on aflatoxin $B_1$ production. In conclusion, we believe that they might be an agent for the control of mycotoxin in agricultural commodities.

• Journal of Photoscience
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• v.12 no.2
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• pp.109-111
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• 2005

It was found that 1,4-diketones such as 1,4-diphenyl-l,4-butanediones containing N,N-dimethylaminophenyl (pDPB) and N,N-dimethylaminonaphthyl (nDPB) at C2 are converted into 3-(4-dimethylaminoaryl)-1-phenylpropan-lones (pPPA and nPPA) by treatment with $Ca(OH)_2$ in methanol, which was easily oxidized to enone, i.e., 3-(4-dimethylaminophenyl)-l-phenylpropenones (pPPE and nPPE), when treated with 2,3-dichloro-5,6-dicyano-l,4-benzoquinone (DDQ) in dichloromethane.

• Bulletin of the Korean Chemical Society
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• v.31 no.6
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• pp.1689-1694
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• 2010

Substituent chemical shifts were examined for the 2- and 3-thiophene derivatives of chalcone and compared to the thiophene series of derivatives with the phenyl series. The chemical shift values for the ${\alpha}$-carbons of the enones showed and inverse correlation with the Hammett $\sigma$ values, but the correlation coefficients were moderate (r = 0.836 - 0.878). On the other hand, the $\beta$-carbons showed a normal correlation with excellent correlation coefficients (r = 0.994). The absolute magnitude of the $\rho$ values for the $\alpha$-carbon are about half of those of the $\beta$-carbon. The observation may be the result of a through-space transition of the electronic effect of the substituents in addition to the through bond transition.

• Bulletin of the Korean Chemical Society
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• v.23 no.4
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• pp.587-592
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• 2002

Photocrosslinkable chalcone-epoxy compound comprising 1,3-bis-(4-hydroxy-phenyl)-propenone was synthe-sized for fabricating the photo-alignment layer of liquid crystals. Chalcone group was introduced into the main chain unit of the epoxy oligomer. We observed a photodimerization behavior and an optical anisotropy of this material by irradiation of a linearly polarized UV(LP-UV) light. With a trace amount of cationic photoinitiator (TRS-HFA), polymerization of epoxy groups was also conducted at the similar wavelength range used for photodimerization. Linearly polarized UV irradiation on the chalcone-epoxy films with cationic photoinitiator induced optical anisotropy of the film and the resultant film can be used for alignment layers for low molecular weight nematic liquid crystals.

• Biomolecules & Therapeutics
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• v.24 no.6
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• pp.595-603
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• 2016

(E)-3-Phenyl-1-(2-pyrrolyl)-2-propenone (PPP) is a pyrrole derivative of chalcone, in which the B-ring of chalcone linked to ${\beta}$-carbon is replaced by pyrrole group. While pyrrole has been studied for possible Src inhibition activity, chalcone, especially the substituents on the B-ring, has shown pharmaceutical, anti-inflammatory, and anti-oxidant properties via inhibition of NF-${\kappa}B$ activity. Our study is aimed to investigate whether this novel synthetic compound retains or enhances the pharmaceutically beneficial activities from the both structures. For this purpose, inflammatory responses of lipopolysaccharide (LPS)-treated RAW264.7 cells were analyzed. Nitric oxide (NO) production, inducible NO synthase (iNOS) and tumor necrosis factor-${\alpha}$ (TNF-${\alpha}$) mRNA expression, and the intracellular inflammatory signaling cascade were measured. Interestingly, PPP strongly inhibited NO release in a dose-dependent manner. To further investigate this anti-inflammatory activity, we identified molecular pathways by immunoblot analyses of nuclear fractions and whole cell lysates prepared from LPS-stimulated RAW264.7 cells with or without PPP pretreatment. The nuclear levels of p50, c-Jun, and c-Fos were significantly inhibited when cells were exposed to PPP. Moreover, according to the luciferase reporter gene assay after cotransfection with either TRIF or MyD88 in HEK293 cells, NF-${\kappa}B$-mediated luciferase activity dose-dependently diminished. Additionally, it was confirmed that PPP dampens the upstream signaling cascade of NF-${\kappa}B$ and AP-1 activation. Thus, PPP inhibited Syk, Src, and TAK1 activities induced by LPS or induced by overexpression of these genes. Therefore, our results suggest that PPP displays anti-inflammatory activity via inhibition of Syk, Src, and TAK1 activity, which may be developed as a novel anti-inflammatory drug.