• Archives of Pharmacal Research
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• 제29권11호
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• pp.969-976
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• 2006

Novel chalcones were found as potent inhibitors of interleukin-5 (II-5). 1-(6-Benzyloxy-2-hydroxyphenyl)-3-(4-hydroxyphenyl)propenone (2a, 78.8% inhibition at $50\;{\mu}M,\;IC_{50}=25.3\;{\mu}M$) was initially identified as a potent inhibitor of IL-5. This activity is comparable to that of budesonide or sophoricoside (1a). The benzyloxy group appears to be critical for the enhancement of the IL-5 inhibitory activity. To identify the role of this hydrophobic moiety, cyclohexyloxy (2d), cyclohexylmethoxy (2c), cyclohexylethoxy (2e), cyclohexylpropoxy (2f), 2-methylpropoxy (2g), 3-methylbutoxy (2h), 4-methylpentoxy (2i), and 2-ethylbutoxy (2j) analogs were prepared and tested for their effects on IL-5 bioactivity. Compounds 2c ($IC_{50}=12.6\;{\mu}M$), 2d ($IC_{50}=12.2\;{\mu}M$), and 2i ($IC_{50}=12.3\;{\mu}M$) exhibited the most potent activity. Considering the cLog P values of 2, the alkoxy group contributes to the cell permeability of 2 for the enhancement of activity, rather than playing a role in ligand motif binding to the receptor. The optimum alkoxy group in ring A of 2 should be one that provides the cLog P of 2 in the range of 4.22 to 4.67.

• 대한화학회지
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• 제58권5호
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• pp.496-499
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• 2014

• Bulletin of the Korean Chemical Society
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• 제24권10호
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• pp.1425-1426
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• 2003

• 대한화학회지
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• 제56권2호
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• pp.246-250
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• 2012

An efficient access, single step and environmentally benign synthesis of a new series of pyrazole containing isoxazolines derivatives were prepared by the condensation of chalcones bearing pyrazole moiety with hydroxyl amine hydrochloride in basic condition by using polyethylene glycol-400 (PEG) as a greener reaction solvent. The advantages of the present methodology are mild reaction condition and avoidance of volatile organic solvent. Furthermore, these newly synthesized compounds were screened for their antimicrobial activity against various pathogens like Escherichia coli (MTCC 2939), Salmonella typhi (MTCC 98), Staphylococcus aureus (MTCC 96), Bacillus subtilis (MTCC 441), Aspergillus niger (MTCC 281), Aspergillus flavus (MTCC 2501), Penicillium chrsogenum (MTCC 160) and Fusarium moniliformae (MTCC 156). Especially compound containing the hydroxyl group in C2-position and presence of halo (I, Br and Cl) groups as substituents at $C_3$ and $C_5$ position on the benzene nucleus showed the higher activity. Furthermore, compounds bearing methyl groups in combination with I and Br which enhanced the activity.

• 대한화학회지
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• 제51권2호
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• pp.115-124
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• 2007

α, β-불포화 케톤 유도체를 실리카-황산 촉매 하에서 비용매 교차 알돌 응축 반응법을 이용하여 합성하였다. 합성 수율은 90% 이상이었으며, 사용된 촉매는 회수 가능하였다. 합성돤 화합물들의 물리화학적인 특성은 IR, NMR, Mass 등의 분광학적 분석 방법을 이용하여 결정하였다. 케톤 생성물에 미치는 치환기 효과는 측정된 분광 데이터와 Hammet 치환기 상수간의 상관관계로 표현되는 다중 상관계수 방정식에 의하여 잘 설명될 수 있었다.

• 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.

• 대한화학회지
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• 제50권3호
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• pp.183-189
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• 2006

초음파를 이용한 응축 반응을 이용하여 다양한 치환기가 붙은 4-methoxy-1-naphthyl ketone화합물들을 90% 이상의 높은 수율로 합성하였으며, 생성된 화합물물들을 미세 분석법, IR, 1H, 13C NMR 분석법 등을 이용하여 확인하였다. IR 스펙트럼에서 s-cis와 s-trans C=O stretching 모드를 확인하였으며, NMR 데이터로부터 에틸렌의 탄소와 수소에 대한 chemical shift를 확인하였다. 이러한 분광데이터를 이용하여 여러 분자들에 대한 Hammet 치환기 상수 값 들을 얻을 수 있었으며, 이들로부터 가용매 분해반응에 미치는 치환기 효과를 해석할 수 있었다.

• Bulletin of the Korean Chemical Society
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• 제24권4호
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• pp.426-430
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• 2003

A range of methine dyes has been synthesized by condensation of highly electronegative active methylene compound dicyanomethylenecyclopentane derived from cyclopentanone with the formyl group of substituted benzaldehydes. The electronic absorption spectroscopic properties of the dyes were investigated. In general, substituents on the aromatic aldehyde moiety have a significant effect on the visible absorption maxima of the dyes; increasing the solvent polarity also showed a pronounced effect on the absorption maxima.

• 약학회지
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• 제10권2_3호
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• pp.12-14
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• 1966

한얀 40종에 대하여 식물화학적 조사를 하고 그중 알카로이드의 존재를 Thin layer chromatography로 검출한 결과를 보고한다.

• Bulletin of the Korean Chemical Society
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• 제34권3호
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• pp.875-883
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• 2013

Ten new derivatives of 1,3-diazabicyclo[3.1.0]hex-3-enes linked via ether linkage to chalcones were synthesized and characterized by UV, FT-IR, $^1H$ NMR and $^{13}C$ NMR spectral techniques. The spectra of all synthesized compounds, confirmed structure-photochromic behavior relationships (SPBR) both in solution or in solid state by irradiation under UV light at 254 nm. In other efforts for first time photochromic behavior of ketoaziridines has been investigated.