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KMID : 0604520140400040383
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Journal of the Society of Cosmetic Scientists of Korea
2014 Volume.40 No. 4 p.383 ~ p.390
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2D-QSAR Analyses on The Tyrosinase Inhibitory Activity of 2-[(2,6-Dioxocyclohexyl)methyl]-cyclohexane-1,3-dione Analogues
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Kim Sang-Jin
Sung Nack-Do
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Abstract
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The following conclusion was made from the 2D-QSAR model for the tyrosinase inhibitory activity according to the variation of the substituents R1 and R2 in analogues of compound 2-[(2,6-dioxocyclohexyl)methyl]cyclohexane- 1,3-dione (1-23). The best optimized 2D-QSAR model was Obs.pI50=-0.295(±0.031)TDM -0.120(±0.014)DMZ+0.135(±0.050)DMX.R2+6.382(±0.17), and the correlation r2=0.905) of which was greater than its predictability (q2=0.843). The magnitude of the effect of tyrosinase inhibitory activities was in order of TDM > DMX.R2≥DMZ, and it tended to increase as the hydrophobicity of substrate molecule (ClogP > 0) as well as the steric favor of substituent R1 increased. The analysis of the model implies that inhibitory activity of substrate molecule will increase as DMX.R2 (Dipole moment X component of R2-substituent) increases, while TDM (Total Dipole Moment) and DMZ(Dipole Moment of Z-Component) decrease. As such, it is deemed feasible to conclude, that in order to increase the inhibitory effect, it would be rather desirable to replace the polar groups within the molecules with non-polar functional groups.
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KEYWORD
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2-[(2, 6-dioxocyclohexyl)methyl]cyclohexane-1, 3-diones, Tyrosinase inhibitory activity, 2D-QSAR model, Total dipole moment, ClogP
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