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Aryldifluoromethylphosphonic acids were transformed into the corresponding phosphonothioic acids via their bis-(2-cyanoethyl) esters for the evaluation of their biological effects on protein tyrosine phosphatase 1B. Difluoro(2-naphthyl)-methylphosphonothioic acid 5d showed better inhibitory potency and higher hydrophobicity than the corresponding difluoromethylenephosphonic acid analogue 1d.

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The difluoromethylenephosphonothioic acid group as a phosphate surrogate for obtaining PTP-1B inhibitors. Transformation of difluoromethylenephosphonic acids into difluoromethylenephosphonothioic acids