Phosphoryloxymethyl Carbamates and Carbonates—Novel Water-Soluble Prodrugs for Amines and Hindered Alcohols

@article{Safadi1993PhosphoryloxymethylCA,
  title={Phosphoryloxymethyl Carbamates and Carbonates—Novel Water-Soluble Prodrugs for Amines and Hindered Alcohols},
  author={Muhammad Safadi and Reza Oliyai and Valentino J. Stella},
  journal={Pharmaceutical Research},
  year={1993},
  volume={10},
  pages={1350-1355}
}
Phosphoryloxymethyl carbonates and carbamates of the type R 1 R 2 X-CO-O-CH2-O-PO3 −2 (X = O or N) were evaluated as potentially novel water-soluble collapsible prodrugs for alcohols and amines. These were prepared by reaction of α-chloromethyl chloroformate with the starting alcohol or amine to give the corresponding α-chloromethyl carbonate or carbamate, respectively. Reaction with silver dibenzyl phosphate followed by debenzylation by hydrogenolysis gave the desired products. The aqueous… CONTINUE READING
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