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Regioselective phosphorylation of tetrahydroxythiacalix[4] arenes by diethyl chlorophosphate in the presence of triethylamine or by the system diethylphosphite/carbon tetrachloride/triethylamine gave ethyl esters of thiacalix[4] arene monophosphoric or thiacalix[4] arene diphosphoric acids, respectively. The obtained esters were converted with quantitative yields into corresponding free acids by sequential treatment with trimethylbromosilane and methanol. The thiacalix[4] arene diphosphoric acids were evaluated in vitro as inhibitors of glutathione S-transferases.

Thiacalix[4]arene phosphoric acids. Synthesis, structure, and inhibition of glutathione S -transferases