Isoxsuprine

4-[1-hydroxy-2-(1-phenoxypropan-2-ylamino)propyl]phenol is an alkylbenzene.|A beta-adrenergic agonist that causes direct relaxation of uterine and vascular smooth muscle. Its vasodilating actions are greater on the arteries supplying skeletal muscle than on those supplying skin. It is used in the treatment of peripheral vascular disease and in premature labor.

To a solution of 30.7 g (0.203 mol) of 1-phenoxy-2-aminopropane in 150 ml of ethanol there was added 31.9 g (0.100 mol) of 1-(4'-benzyloxyphenyl)-2- bromopropanone-1. The mixture was heated to boiling temperature and the solution was then refluxed in a reflux condenser for 3 hours. Most of the ethanol was then distilled off in vacuo, Then to the residue there was addedabout 150 ml of diethyl ether. The hydrogen bromide salt of 1-phenoxy-2- aminopropane was filtered off and washed with diethyl ether. The collected ethereal filtrates were acidified with 50 ml of 4 N hydrochloric acid and this solution was stirred vigorously. The hydrochloride of 1-(4'- benzyloxyphenyl)-2-(1'-methyl-2-phenoxy-ethylamino)propanone-1 precipitated out, was filtered off, washed with water and then with diethyl ether. Then this substance was dried in vacuo. The yield was 37.7 g, i.e., 89% of the theoretically possible yield, calculated on 1-(4'-benzyloxyphenyl)-2- bromine propanone-1. This substance had a light yellow color and melted at 197 to 198°C, while decomposing. Then 21.89 g of the hydrochloride salt was dissolved in 600 ml of 80% aqueous ethanol. With the addition of a palladium carbon catalyst, this solution was hydrogenated at room temperature under a hydrogen pressure of about 1.1 atmospheres. After 2 mols hydrogen had been absorbed, the catalyst was filtered off and the filtrate was evaporated in vacuo until crystallization occurred. Then the crystals were dissolved by heating in the smallest possible quantity of water and after cooling, the crystallized substance was filtered off, washed with water and dried in vacuo. The yield was 6.80 g, i.e., 39% of the theoretically possible yield. The resultant product recrystallized from water melted at 203° to 204°C.

Vasodilator.

Molecular Weight:301.4
XLogP3:2.8
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:7
Exact Mass:301.16779360
Monoisotopic Mass:301.16779360
Topological Polar Surface Area:61.7
Heavy Atom Count:22
Complexity:299
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes