Olprinone

Olprinone(Loprinone) is a selective phosphodiesterase 3 (PDE3) inhibitor. IC50 value:Target: PDE3Olprinone is used as cardiotonic agent with positive inotropic and vasodilating effects. Olprinone has been reported to improve microcirculation and attenuate inflammation. Olprinone is often used to increase cardiac output after cardiopulmonary bypass (CPB). Olprinone was infused at a rate of 0.2 μg/kg/min when weaning from CPB was started. Olprinone has also shown potent antioxidative and a

Olprinone is a member of bipyridines.

13.3 g of compound iii (0.062 mol), 12.1 g of compound vi (0.075 mol), 4.5 g of bis(triphenylphosphine)palladium(II) chloride (0.006 mol), 1.0 mol/L potassium carbonate solution 64ml in argon under the protection of added to 133ml toluene, heated to 90 ~ 100 , incubation reaction 24h. The reaction mixture was poured into 200 ml of purified water, extracted with 70 ml of ethyl acetate three times, twice with 100 ml of saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a pale gray solid which was beaten with petroleum ether for 1 hour to give an off-white solid, i.e., Oprinon (compound ii), and weighed 11.2 g in a yield of 71.7percent.To a 250 mL three-necked flask, Intermediate IV 9.82 g, methanol 39 mL, and purified water 118 mL were added, and the mixture was stirred and warmed. The temperature was controlled at 70-80 C, 6.5 mL of concentrated hydrochloric acid was added dropwise, the solid was completely dissolved, and the temperature was kept for 10 min, and the temperature was lowered to room temperature. The solid was precipitated, suction filtered, and the filter cake was washed with a small amount of water, and dried at 45 C for 1 h to obtain a pale yellow solid of 11.32 g. It is a crude crude product of apricot hydrochloride with a yield of 94.7%.To a 250 mL three-necked flask, 10.00 g of crude aprenamine hydrochloride was added, and 110 mL of purified water was added thereto, and the mixture was heated to 85 C with stirring, completely dissolved, kept for 10 minutes, and lowered to room temperature. The filter cake was suction filtered, and the filtrate was washed with a small amount of purified water, and dried at 40 C for 1 hour to obtain an off-white solid of 8.46 g. The yield was 84.6%.11.0 g of compound ii (0.044 mol) was added to 110 ml of DMF, heated to 80 C, and 9 ml of a mixed solution of concentrated hydrochloric acid and ethanol was added dropwise to the reaction flask (concentrated hydrochloric acid: ethanol = 1: 1), and the mixture was stirred at 80 C for 1 h. Stop heating, cooling crystallization, the crystal filter, add 165ml methanol - water (2: 1)Heating to reflux, adding activated carbon stirring decolorization, hot filter mother liquor cooling stirring and recrystallization, filtered white solid, that is, 13.3 g of compound iii (0.062 mol), 12.1 g of compound vi (0.075 mol), 4.5 g of bis(triphenylphosphine)palladium(II) chloride (0.006 mol), 1.0 mol/L potassium carbonate solution 64ml in argon under the protection of added to 133ml toluene, heated to 90 ~ 100 , incubation reaction 24h. The reaction mixture was poured into 200 ml of purified water, extracted with 70 ml of ethyl acetate three times, twice with 100 ml of saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a pale gray solid which was beaten with petroleum ether for 1 hour to give an off-white solid, i.e., Oprinon (compound ii), and weighed 11.2 g in a yield of 71.7%.To a 500 mL three-necked flask, Intermediate III 12.78 g, 166 mL of absolute ethanol, 6.98 g of cyanoacetamide (SM4), and 6.02 g of sodium methoxide were successively added, and the mixture was heated to reflux with stirring, and the reaction was kept for 1 h. The reaction was monitored by TLC, and the disappearance of the spot of the intermediate III was regarded as the end of the reaction (developing agent = dichloromethane: methanol = 10:1). At room temperature, 64 mL of purified water was added, about 7 mL of glacial acetic acid was added slowly, pH was adjusted to 7-8, solids were precipitated, stirred at room temperature for 1 h, suction filtered, washed with a small amount of ethanol, and the filter cake was dried at 45 C for 1 h to obtain a yellow solid 12.26. g, intermediate IV, yield 87.9%.

Used to treat acute myocardial insufficiency.

Molecular Weight:250.25
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:250.08546096
Monoisotopic Mass:250.08546096
Topological Polar Surface Area:70.2
Heavy Atom Count:19
Complexity:525
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes