First synthesis of α-aminoalkyl-(N-substituted)thiocarbamoyl-phosphinates: Inhibitors of aminopeptidase N (APN/CD13) with the new zinc-binding group

OO-Di-trimethylsilyl esters of α-N-benzyloxycarbonylaminoalkylphosphinates (III) undergo triethylamine catalyzed addition to isothiocyanates to give after hydrolysis, a series of new α-aminoalkyl-(N-substituted)thiocarbamoyl-phosphinates. Thiocarbamoyl-phosphinate moiety can be included in the structures of the metalloproteinase inhibitors as the zinc-binding group and the new compounds reported here are good inhibitors of important aminopeptidase N(CD13) with IC50 in range of 10.56–0.25 μM.