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KMID : 0043320080310121540
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Archives of Pharmacal Research
2008 Volume.31 No. 12 p.1540 ~ p.1546
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CoMFA on the Melanogenesis Inhibitory Activity of Alkyl-3,4-dihydroxybenzoate, N-Alkyl-3,4-dihydroxybenzamide Analogues, and Prediction of Higher Active Compounds
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Sung Nack-Do
Myung Pyung-Keun
Kim Sang-Jin
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Abstract
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To predict a new materials of superior melanogenesis inhibitory activities (MIA), the comparative molecular field analysis (CoMFA) models on MIA of alkyl-3,4-dihydroxybenzoates and N-alkyl-3,4- dihydroxybenzamides analogues against mouse melanoma cell were derived and discussed quantitatively. The optimized CoMFA model II from the field fit alignment demonstrated better predictability of molecular structure with the non-cross validated conventional coefficient (r2ncv.=0.984) and cross-validated coefficient (r2 cv. or q=0.706) than that from atom based fit alignment. Also, the relative contribution of the optimized CoMFA model II showed the steric (63.8%), electrostatic (18.4%), and hydrophobic (ClogP) field (17.8%), respectively. The results indicated that the esters (alkyl-3,4-dihydroxybenzoates) are more active inhibitors than the amides (N-alkyl-3,4-dihydroxybenzamides). Furthermore, the optimized CoMFA model II is proven to be a useful approach to design a highly active melanogenesis inhibitor molecules, and enables to predict R1=n-dodecy and R2=n-heptyloxy substituted compound of alkyl-3,4-dihydroxybenzoates as the most active compounds (Pred. pI50=5.87).
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KEYWORD
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Alkyl-3, 4-dihydroxybenzoates, N-alkyl-3, 4-dihydroxybenzamides, Comparative molecular field analysis (CoMFA), Melanogenesis inhibitory activity (MIA)
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