• Bulletin of the Korean Chemical Society
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• 제33권8호
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• pp.2585-2591
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• 2012

A series of heterocyclic chalcone derivatives bearing heterocycles such as thiophene or furan ring as an isostere of benzene ring were carefully prepared, and the influence of heterocycles on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities was systematically investigated. Structure-activity relationships (SAR) analysis showed that the activities of thiophene ring-containing chalcones were higher than those of furan ring-containing chalcones, and the presence of methyl substituent of heterocyclic ring distinctly affected the activities compared with non-substituted heterocycles in an opposite manner, with the 4'-methyl group of thiophene ring increasing activity and the 3'-methyl group of the furan ring decreasing activity. The distinct isosteric effect of heterocycles (i.e., thiophene or furan ring) on radical scavenging activities of heterocyclic chalones was distinctly demonstrated in our work.

• Applied Biological Chemistry
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• 제43권2호
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• pp.95-99
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• 2000

일련의 헤테로 고리 치환(X) chalcone 유도체들에 의한 farnesyl protein transferase(FPTase) 저해활성을 측정하여 분자내 styryl group의 치환기(Y) 변화에 따른 정량적인 구조와 FPTase 저해 활성과의 관계(QSARs)를 modified Free-Wilson(F-W)방법 및 Hansch 방법으로 분석 검토하였다. F-W 분석에 따르면 (X)-치환기는 FPTase 저해 활성에 기여하지 않았다 그러나 (Y)-치환기들은 ortho>meta>para 치환체의 순서로 ortho-치환체와 ${\alpha}$탄소의 알짜 전하$(C_{\alpha})$가 활성에 기여하였다. 모든 헤테로 고리 치환체에 대한 Hansch 분석에 의하면 전자 밀게(R<0)의 폭$(B_1)$이 작은 ortho-치환체로서 적정값, $(R)_{opt.}=-0.35$를 갖는 공명상수가 저해활성에 영향을 미친다는 사실을 알 수 있었다. 그리고 헤테로 치환체들 사이의 FPTase 저해활성은 모두 비례관계를 보임으로써 같은 경향으로 저해활성이 발현되었으며 비(H)치환체 45가 제일 높은 FPTase 저해활성$(pI_{50}=4.30)$을 보였다.

• Bulletin of the Korean Chemical Society
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• 제32권9호
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• pp.3459-3464
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• 2011

In order to extend the scaffold of non-peptidic calpain inhibitor, we have designed and synthesized 14 chalcone derivatives categorized into two groups based on their structures. Compounds 7 ($IC_{50}=16.67{\pm}0.42{\mu}M$) and 8 ($IC_{50}=16.92{\pm}0.14{\mu}M$) in group A were most selective ${\mu}$-calpain inhibitor over cathepsins B and L. On the other hand, compound 14 possessing furan ring exhibited inhibitory activities for ${\mu}$-calpain ($IC_{50}=15.39{\pm}1.34{\mu}M$) as well as cathepsin B ($IC_{50}=20.59{\pm}1.35{\mu}M$). The results discovered implicated that chalcone analogues possessing proper size and functional groups can be a potential lead core for selective non-peptidic ${\mu}$-calpain inhibitor. Furthermore, dual inhibitors for ${\mu}$-calpain and cathepsin B can also be developed from chalcones by elaborate structure manipulation.

• BMB Reports
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• 제44권11호
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• pp.730-734
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• 2011

Amyloid ${\beta}$-peptide ($A{\beta}$-peptide)-induced oxidative stress is thought to be a critical component of the pathophysiology of Alzheimer's disease (AD). New chalcone derivatives, the Chana series, were recently synthesized from the retrochalcones of licorice. In this study, we investigated the protective effects of the Chana series against neurodegenerative changes in vitro and in vivo. Among the Chana series, Chana 30 showed the highest free radical scavenging activity (90.7%) in the 1,1-diphenyl-2- picrylhydrazyl assay. Chana 30 also protected against $A{\beta}$-induced neural cell injury in vitro. Furthermore, Chana 30 reduced the learning and memory deficits of $A{\beta}_{1-42}$-peptide injected mice. Taken together, these results suggest that Chana 30 may be a promising candidate as a potent therapeutic agent against neurodegenerative diseases.

• Bulletin of the Korean Chemical Society
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• 제34권4호
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• pp.1023-1024
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• 2013

• Bulletin of the Korean Chemical Society
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• 제32권1호
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• pp.65-70
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• 2011

Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by $TiCl_4$. This method can be used for preparing various coumarin & chalcone compounds.

• Biomolecules & Therapeutics
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• 제26권2호
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• pp.191-200
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• 2018

Chalcone, (2E)-1,3-Diphenylprop-2-en-1-one, and its synthetic derivatives are known to possess anti-oxidative and anti-inflammatory properties. In the present study, we prepared a novel synthetic chalcone compound, (E)-1-(4-hydroxyphenyl)-3-(2-(trifluoromethoxy)phenyl)prop-2-en-1-one name (YJI-7), and investigated its inhibitory effects on endotoxin-stimulated production of reactive oxygen species (ROS) and expression of inflammatory mediators in macrophages. We demonstrated that treatment of RAW 264.7 macrophages with YJI-7 significantly suppressed lipopolysaccharide (LPS)-stimulated ROS production. We also found that YJI-7 substantially decreased NADPH oxidase activity stimulated by LPS, indicating that YJI-7 regulates ROS production via modulation of NADPH oxidase in macrophages. Furthermore, YJI-7 strongly inhibited the expression of a number of inflammatory mediators in a gene-selective manner, suggesting that YJI-7 possesses potent anti-inflammatory properties, as well as anti-oxidative activity. In continuing experiments to investigate the mechanisms that could underlie such biological effects, we revealed that YJI-7 suppressed phosphorylation of p38MAPK and JNK stimulated by LPS, whereas no significant effect on ERK was observed. Furthermore, LPS-stimulated production of ROS, activation of NADPH oxidase and expression of inflammatory mediators were markedly suppressed by treatment with selective inhibitor of p38MAPK (SB203580) and JNK (SP600125). Taken together, these results demonstrated that YJI-7, a novel synthetic chalcone derivative, suppressed LPS-stimulated ROS production via modulation of NADPH oxidase and diminished expression of inflammatory mediators, at least in part, via down-regulation of p38MAPK and JNK signaling in macrophages.

• Archives of Pharmacal Research
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• 제13권4호
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• pp.347-350
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• 1990

The hydrazine derivative 2 has been utilized for the synthesis of three different fused 1, 2, 4-triazolo [4, 3-a] pyrimidine derivatives 4, 5, &6 and a tetrazolo [1, 5-a] pyrimidine derivative 7. Reaction of 2 with the chalcone analogue 2-thenylidene-2'-acetothienone, gave the pyrazoline derivative 8.

• Bulletin of the Korean Chemical Society
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• 제31권6호
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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.

• Natural Product Sciences
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• 제25권1호
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• pp.76-80
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• 2019

Bioactivity-guided fractionation of MeOH extract of the dried fruits of Amomum tsao-ko led to isolation of nine compounds (1 - 9). Their structures were elucidated by spectroscopic methods including extensive 1D and 2D-NMR, as alpinetin (1), naringenin-5-O-methyl ether (2), naringenin (3), hesperetin (4), 2',4',6'-trihydroxy-4-methoxy chalcone (5), tsaokoin (6), boesenbergin B (7), 4-hydroxyboesenbergin B (8), and tsaokoarylone (9). Of these, compound 8 was isolated from a natural source for the first time, which was previously reported as a synthetic product. The isolated compounds (1 - 9) were tested for their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages. Among them, three chalcone derivatives (compounds 5, 7, and 8) and a diarylheptanoid (compound 9) exhibited significant inhibitory activity on the NO production with $IC_{50}$ values ranging from 10.9 to $22.5{\mu}M$.