Mer-29,Merrell National,US,1960
Desmosterol Delta 24 (D24) reductase inhibitor
Triparanol has been used to inhibit cholesterol biosynthesis in lipid rafts1. Triparanol has also been used as a 3β-hydroxysterol-Δ24-reductase inhibitor to study its effect on delayed-rectifier potassium current (Iks) channels2.
ChEBI: Triparanol is a stilbenoid. It has a role as an anticoronaviral agent.
4-(β-diethylaminoethoxy)-4-methylbenzophenone was prepared as follows: a
mixture of 200 g of 4-hydroxy-4-methylbenzophenone, 55 g of powdered
sodium methoxide and 400 ml of ethanol was stirred for 30 minutes. A
solution of 150 g of β-diethylaminoethyl chloride in 300 ml of toluene was
added and the mixture was refluxed four hours. The solvent was removed, the
residue was taken up in ether, extracted with 5% NaOH solution, twice with
water, the ether was removed and the residue was distilled. The product was
obtained as an oil boiling at 232°C at 0.6 mm.
1 liter of a 0.45 N ethereal solution of p-chlorobenzyl magnesium chloride was
added in 30 minutes to a stirred solution of 104 g (0.35 mol) of 4-(β-
diethylaminoethoxy)-4-methylbenzophenone in 400 ml of dry ether. After
stirring an additional hour, the mixture was decomposed by pouring onto 1
liter of cold 10% ammonium chloride solution, the ether solution was washed
with water, and the ether was replaced with hot isopropanol containing a trace
of ammonia. 1-[p-(β-diethylaminoethoxy)phenyl]-1-phenyl-2-p-tolyl-2-p_x0002_chloroethanol separated as white crystals, melting at 104% to 106°C.
Triparanol is known to repress Hedgehog signaling in cancer cells and can also inhibit tumor growth3.
