An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide. synthesis and preliminary biological studies

Bioorg Med Chem Lett. 2001 Jun 18;11(12):1583-6. doi: 10.1016/s0960-894x(01)00230-x.


The synthesis of a nonhydrolyzable, carbon-linked analogue (4-HBR) of the retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) using Umpolung methods is described. Preliminary studies of biological activity show 4-HBR is similar to 4-HPR in its actions although a potentially relevant and desirable difference is its reduced suppression of plasma vitamin A levels. These results show that 4-HPR does not have to be hydrolyzed to retinoic acid to produce its chemotherapeutic effects.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacokinetics*
  • Antineoplastic Agents / pharmacology
  • Biotransformation
  • Female
  • Fenretinide / analogs & derivatives*
  • Fenretinide / chemical synthesis
  • Fenretinide / pharmacokinetics*
  • Fenretinide / pharmacology
  • Hydrolysis
  • Mammary Neoplasms, Experimental / drug therapy
  • Rats
  • Vitamin A / blood


  • Antineoplastic Agents
  • Vitamin A
  • Fenretinide