Antifertility agents. 12. Structure-activity relationship of 3,4-diphenylchromenes and -chromans

J Med Chem. 1976 Feb;19(2):276-9. doi: 10.1021/jm00224a014.

Abstract

Synthesis and antiimplantation activity of variously substituted 2,2-dialkyl-3,4-diphenylchromenes and 3,4-cis- and trans-chromans derived from them are described. Pregnancy-inhibiting activity in rats was exhibited by a number of these compounds, which was particularly marked in the case of 3,4-trans-3-phenyl-4-p-(beta-pyrrolidinoethoxy)-phenyl-7-methoxychroman (32), the corresponding 2,2-dimethyl analog 34, and 3-phenyl-4-p-(beta-pyrrolidinoethoxy)phenyl-7-methoxychromene (26). The structure-activity relationship of these compounds is discussed.

MeSH terms

  • Animals
  • Benzopyrans / chemical synthesis*
  • Chromans / chemical synthesis*
  • Chromans / pharmacology
  • Contraceptives, Oral / chemical synthesis*
  • Contraceptives, Oral, Synthetic / chemical synthesis*
  • Depression, Chemical
  • Embryo Implantation / drug effects
  • Estrogens
  • Female
  • Fertility / drug effects*
  • Fetal Resorption / chemically induced
  • Organ Size / drug effects
  • Pregnancy
  • Rats
  • Structure-Activity Relationship
  • Uterus / drug effects

Substances

  • Benzopyrans
  • Chromans
  • Contraceptives, Oral
  • Contraceptives, Oral, Synthetic
  • Estrogens