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KMID : 0043320060290110969
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Archives of Pharmacal Research
2006 Volume.29 No. 11 p.969 ~ p.976
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The Role of the Hydrophobic Group on Ring A of Chalcones in the Inhibition of Interleukin-5
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Yang Hyun-Mo
Shin Hye-Rim
Cho Soo-Hyun
Song Gyu-Yong
Lee In-Jeong
Kim Mi-Kyeong
Lee Seung-Ho
Ryu Jae-Chun
Kim Young-Soo
Jung Sang-Hun
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Abstract
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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 ) 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 (), 2d (), and 2i () 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.
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KEYWORD
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Chalcones, Inhibitor, Interleukin-5
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