ChemicalBook--->CAS DataBase List--->74258-86-9

74258-86-9

74258-86-9 Structure

74258-86-9 Structure
IdentificationMore
[Name]

Alacepril
[CAS]

74258-86-9
[Synonyms]

ALACEPRIL
(s)-l-phenylalanin
1-(d-3-acetylthio-2-methylpropanoyl)-l-prolyl-l-phenylalanine
cetapril
du1219
L-Phenylalanine, 1-[(2S)-3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl-
L-Phenylalanine, N-[1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl]-, (S)-
2-[[1-(3-Acetylsulfanyl-2-methylpropanoyl)pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid
(S)-N-[1-[3-(Aeetylthio)-2-methyl-1-oxopropyl]-L-prolyl]-L-phenylalanine
Cetapfil
1-[(S)-3-Acetylthio-2-methylpropanoyl]-L-Pro-L-Phe-OH
N-[(S)-3-Acetylthio-2-methylpropanoyl]-L-Pro-L-Phe-OH
N-[1-[(S)-3-(Acetylthio)-2-methyl-1-oxopropyl]-L-prolyl]-L-phenylalanine
[Molecular Formula]

C20H26N2O5S
[MDL Number]

MFCD00869538
[Molecular Weight]

406.5
[MOL File]

74258-86-9.mol
Chemical PropertiesBack Directory
[Melting point ]

155-156°
[alpha ]

D25 -81.3° (c = 1.02 in ethanol)
[storage temp. ]

2-8°C
[CAS DataBase Reference]

74258-86-9(CAS DataBase Reference)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Trifluoroacetic acid-->Anisole-->4-Methylmorpholine-->Amyl acetate-->Sodium bicarbonate-->Hydrochloric acid-->1-(D-3-ACETYLTHIO-2-METHYLPROPANOYL)-L-PROLINE-->Phenyl chloroformate-->tert-Butyl 3-phenyl-L-alaninate hydrochloride
Hazard InformationBack Directory
[Description]

Alacepril is an angiotensin-converting enzyme (ACE) inhibitor useful in the treatment of essential and renal hypertension. Compared with captopril, alacepril is a weaker ACE inhibitor in vino, yet clinically it has a longer duration of action and appears to be more active due to an added component of norepinephrine antagonism.
[Originator]

Dainippon (Japan)
[Definition]

ChEBI: Alacepril is a thioacetate ester and a dipeptide. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor.
[Manufacturing Process]

N-Methylmorpholine (1.03 g) was added to a solution of 1-(D-3-acetylthio-2- methylpropanoyl)-L-proline (2.65 g) in dry tetrahydrofuran (50 ml). The resulting solution was stirred and cooled at -20° to -15°C. Phenyl chloroformate (1.61 g) was added, and after 5 min, a solution of Lphenylalanine t-butyl ester hydrochloride (2.4 g) and N-methylmorpholine (1.03 g) in dry tetrahydrofuran (30 ml) was added. The mixture was stirred at -20° to -15°C for 1 h and then at room temperature overnight.
After removal of insoluble materials by filtration, the filtrate was concentrated under reduced pressure and the residue was dissolved in chloroform.
The chloroform solution was washed successively with 1 N sodium hydroxide, water, 10% citric acid, and water, dried and concentrated under reduced pressure. The residue was chromatographed on silica gel with chloroformmethanol (99:1) to give 4.2 g the 1-(D-3-acetylthio-2-methylpropanoyl)-Lprolyl- L-phenylalanine tert-butyl ester.
1-(D-3-Acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine tert-butyl ester (2.5 g) was dissolved in a mixture of anisole (18 ml) and trifluoroacetic acid (37 ml). The solution was allowed to stand at room temperature for 1 h and then concentrated to dryness under reduced pressure. The residue was crystallized from diethyl ether. The 1-(D-3-acetylthio-2-methylpropanoyl)-Lprolyl- L-phenylalanine was obtained (1.8 g), melting point 155°-156°C (recrystallization from ethanol/n-hexane).
[Brand name]

Cetapril
[Therapeutic Function]

Antihypertensive
Safety DataBack Directory
[Toxicity]

LD50 in rats, mice (mg/kg): >5000, >5000 orally; >3000, >3000 s.c.; ~2000, ~3000 i.p. (Iida, pp 7033-40)
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