179895-47-7

Upstream product

• 179898-11-4 2-Fluoro-8-nitro-benzo[c]chromen-6-one 
• 179895-41-1 9-Fluoro-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-aza-chrysen-5-one 
• 179898-09-0 methyl (5'-fluoro-2'-methoxy-4-nitro-2-biphenyl)carboxylate 
• 179898-10-3 5'-fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylic acid 
• 6942-36-5 methyl 2-bromo-5-nitrobenzoate 
• 54932-72-8 2-chloro-5-bromotoluene 

Relevant academic research and scientific papers

Preparation, resolution, and biological evaluation of 5-aryl-1,2- dihydro-5H-chromeno[3,4-f]quinolines: Potent, orally active, nonsteroidal progesterone receptor agonists

Two potent nonsteroidal progestins from the 5-aryl-1,2-dihydro-5H- chromeno[3,4-f]quinoline class (LG120746 and LG120747) were selected for scale-up, resolution, and biological evaluation of the purified enantiomers. For each quinoline, the levorotatory enantiomer was determined to be the more potent agonist of the human progesterone receptor isoform B (hPR-B) (EC50 50 200 nM). In two in vivo rodent models of progestational activity, a pregnancy maintenance assay and a uterine wet weight assay, the two eutomers displayed potent progesterone-like effects. In a third model for progestational activity, the mammary end bud assay, these compounds were significantly less active. These studies demonstrate that certain members of this class of selective progesterone receptor modulators display encouraging and potentially useful tissue-selective progestational effects.

5-aryl-1,2-dihydro-5H-chromeno[3,4-f]quinolines as potent, orally active, nonsteroidal progesterone receptor agonists: The effect of D-ring substituents

Several 5-(4-chlorophenyl)-1,2-dihydro-5H-chromeno[3,4-f]quinolines were prepared to determine the effects of substitution at C(8) and C(9) on the progestational activity of this pharmacophore. In combination with a halogen (F or Cl) at C(9), replacement of the C(5) aryl group with variously substituted aryl groups resulted in optimization of the progestational activity, affording compounds with in vitro activity greater than that of progesterone as measured by a cotransfection assay using human progesterone receptor subtype-B (hPR-B). Binding affinities (K(i)) to hPR-A were subnanomolar in many cases. These in vitro effects were verified in vivo using a rodent model. Compound 10 (LG120794, 9-chloro-5-(4-chlorophenyl)- 1,2-dihydro-2,2,4-trimethyl-5H-chromeno[3,4-f]quinoline) was more potent than medroxyprogesterone acetate at counterpoising the effects of estradiol benzoate in the uterine wet weight assay using immature rats.