Cycloserine fatty acid derivatives as prodrugs: synthesis, degradation and in vitro skin permeability.

@article{Thorsteinsson2002CycloserineFA,
  title={Cycloserine fatty acid derivatives as prodrugs: synthesis, degradation and in vitro skin permeability.},
  author={Thorsteinn Thorsteinsson and M{\'a}r M{\'a}sson and Tomi Jarvinen and Tapio Nevalainen and Thorsteinn Loftsson},
  journal={Chemical & pharmaceutical bulletin},
  year={2002},
  volume={50 4},
  pages={554-7}
}
Various 4,5-dihydroisoxazol-3-yl fatty acid ester derivatives of cycloserine were synthesized to improve skin permeation of cycloserine. The ester derivatives were prepared by using the tert-butoxycarbonyl (t-Boc) protection strategy. The 4,5-dihydroisoxazol-3-yl esters were readily hydrolysed in an aqueous buffer solution, and the degradation profiles showed both specific acid and specific base catalysis. In 50% human serum the formation of cycloserine was observed, but enzymatic catalysis was… CONTINUE READING

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