Characterization and application of hydrophobic functionalities bearing heavier group 14 atoms

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Systematic synthesis and characterization of simple phenols bearing a trialkyl(aryl)silyl or trialkyl(aryl)germyl functional group as a hydrophobic substituent were investigated. These silicon and germanium analogs exhibited higher hydrophobicity than the corresponding carbon analogs, with a difference in logP value of approximately 0.6, independent of the alkyl(aryl) species. The trialkylsilyl- and trialkylgermylphenols exhibited more potent estrogenic activity as compared with the carbon analogs. The substituent parameters and structure-activity relationship may be helpful for drug discovery utilizing the heavier group 14 elements.