Formal synthesis of the ACE inhibitor benazepril x HCl via an asymmetric aza-Michael reaction.
نویسندگان
چکیده
A formal enantioselective synthesis of benazepril.HCl (4), an anti- hypertensive drug, is reported. Our synthesis employed an asymmetric aza-Michael addition of L-homophenylalanine ethyl ester (LHPE, 1) to 4-(2-nitrophenyl)-4-oxo- but-2-enoic acid methyl ester (6) as the key step to prepare (2S,3'S)-2-(2-oxo-2,3,4,5- tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester (8), which is the key intermediate leading to benazepril x HCl (4).
منابع مشابه
Synthesis, characterization and using Fe3O4@SiO2@FeCl3 as a new nanocatalyst for aza-Michael reaction between amines and ethyl crotonate
In this article, recyclable Fe3O4@SiO2@FeCl3 was synthesized and entirely characterized by various techniques including XRD, FT-IR, SEM, EDX and VSM analysis. The catalytic ability of produced Fe3O4@SiO2@FeCl3 was studied in the aza-Michael reaction of diethyl amine and ethyl crotonate which lead to high yie...
متن کاملAn Efficient Protocol for the Synthesis of Carboacyclic Nucleosides via Aza-Conjugate Addition Reaction
A new efficient method for the synthesis of carboacyclic nucleosides as biologically interesting compounds via aza-conjugate addition of pyrimidine nucleobases to a,β-unsaturated esters in the presence of catalytic amount of LiOH.H2O (1.2-4.8 mol%) under microwave irradiation is described. This method affords the title compounds in good to excellent yields and i...
متن کاملRenoprotection by Telmisartan versus Benazepril in Streptozotocin Induced Diabetic Nephropathy
Diabetic nephropathy (DN) is one of the major causes of end stage renal disease. Angiotensin converting enzyme (ACE) inhibitor and angiotensin receptor blocker (ARB) are preferred for delaying progression of DN. This study compared the preventive renal effects of telmisartan (10 mg/kg, p.o.), an ARB that completely blocks angiotensin action, and benazepril (5 mg/kg, p.o.), an ACE inhibitor, whi...
متن کاملAsymmetric Synthesis of New Diastereomerically Pure Spiro Oxindolopyrrolizidines and Oxindolopyrrolidines via Cycloaddition Reactions of Azomethine Ylides and Menthol-Drived Trans-Cinnamic
Chiral pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds. Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems. Derivatives of spirooxindole find very wide biological applications as anti micr...
متن کاملAsymmetric Synthesis of New Diastereomerically Pure Spiro Oxindolopyrrolizidines and Oxindolopyrrolidines via Cycloaddition Reactions of Azomethine Ylides and Menthol-Drived Trans-Cinnamic
Chiral pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds. Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems. Derivatives of spirooxindole find very wide biological applications as anti micr...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Molecules
دوره 11 8 شماره
صفحات -
تاریخ انتشار 2006