Synthesis and antifertility activity of 3,9-dihydroxy-5,6,6a alpha,6b beta,11,12,12a beta,12b alpha-octahydrodibenzo[a,g]biphenylene, a structural relative of diethylstilbestrol

J Med Chem. 1980 Dec;23(12):1410-4. doi: 10.1021/jm00186a023.

Abstract

The title diphenol, 1a, was synthesized from p,p'-dihydroxy-alpha-truxillic acid and shown to be active as an oral postcoital antifertility agent in rats: ED100 = 100 (micrograms/kg)/day. The oral uterotropic potency was estimated to be 16% of that of diethylstilbestrol (95% confidence limits of potency 8--35%). The structure of the diphenol, 1a, was confirmed by single-crystal X-ray analysis of the dimethyl ether.

Publication types

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

MeSH terms

  • Animals
  • Antineoplastic Agents
  • Chemical Phenomena
  • Chemistry
  • Contraceptives, Postcoital / chemical synthesis*
  • Contraceptives, Postcoital, Synthetic / chemical synthesis*
  • Female
  • Male
  • Naphthols / chemical synthesis*
  • Naphthols / pharmacology
  • Organ Size / drug effects
  • Rats
  • Uterus / drug effects

Substances

  • Antineoplastic Agents
  • Contraceptives, Postcoital
  • Contraceptives, Postcoital, Synthetic
  • Naphthols
  • 3,9-dihydroxyoctahydrodibenzo(a,g)biphenylene