5-Aryl-1,2-dihydrochromeno[3,4-f]quinolines: a novel class of nonsteroidal human progesterone receptor agonists

J Med Chem. 1998 Jan 29;41(3):291-302. doi: 10.1021/jm9705768.

Abstract

The development of a novel class of nonsteroidal human progesterone receptor (hPR) agonists, 5-aryl-1,2-dihydro-5H-chromeno[3,4-f]quinolines 2, is described. The introduction of a 5-aryl group into the 1,2-dihydrocoumarino[3,4-f]quinoline core 1 is the key for progestational activities. The structure-activity relationship (SAR) studies of the 5-aryl substituents generated a series of potent hPR agonists, which exhibited similar biological activity (EC50 = 8-30 nM) to the natural hormone progesterone (EC50 = 2.9 nM) in cell-based assays with efficacies ranging from 28% to 96%. Most of the analogues displayed similar or greater binding affinity (Ki = 0.41-3.6 nM) than progesterone (Ki = 3.5 nM). Three representative analogues (13, 15, and 24) demonstrated in vivo activities in mammary gland morphology/uterine wet weight assay in ovariectomized rats.

MeSH terms

  • Animals
  • Binding, Competitive
  • Female
  • Humans
  • In Vitro Techniques
  • Magnetic Resonance Spectroscopy
  • Mammary Glands, Animal / drug effects
  • Mammary Glands, Animal / metabolism
  • Quinolines / chemistry
  • Quinolines / metabolism
  • Quinolines / pharmacology*
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Androgen / metabolism
  • Receptors, Estrogen / metabolism
  • Receptors, Glucocorticoid / metabolism
  • Receptors, Mineralocorticoid / metabolism
  • Receptors, Progesterone / agonists*
  • Receptors, Progesterone / metabolism
  • Structure-Activity Relationship
  • Uterus / drug effects
  • Uterus / metabolism

Substances

  • Quinolines
  • Receptors, Androgen
  • Receptors, Estrogen
  • Receptors, Glucocorticoid
  • Receptors, Mineralocorticoid
  • Receptors, Progesterone