BIOMAT Database Logo BIOMAT Database Logo

Studies on angiotensin converting enzyme inhibitors. 4. Synthesis and angiotensin converting enzyme inhibitory activities of 3-acyl-1-alkyl-2-oxoimidazolidine-4-carboxylic acid derivatives. 1989

K Hayashi, and K Nunami, and J Kato, and N Yoneda, and M Kubo, and T Ochiai, and R Ishida
Research Laboratory of Applied Biochemistry and Safety Research Laboratory, Tanabe Seiyaku Co., Ltd., Osaka, Japan.

(4S)-1-Alkyl-3-[[N-(carboxyalkyl)amino]acyl]-2-oxoimidazolidine-4- carboxylic acid derivatives (3) were prepared by two methods. Their angiotensin converting enzyme (ACE) inhibitory activities and antihypertensive effects were evaluated, and the structure-activity relationships were discussed. The dicarboxylic acids 3a-n possessing S,S,S configuration showed potent in vitro ACE inhibitory activities with IC50 values of 1.1 X 10(-8)-1.5 X 10(-9) M. The most potent compound in this series, monoester 3p, had an ID50 value of 0.24 mg/kg, po for inhibition of angiotensin I induced pressor response in normotensive rats and produced a dose-dependent decrease in systolic blood pressure of spontaneously hypertensive rats (SHRs) at doses of 1-10 mg/kg, po.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D008297 Male Males
D011918 Rats, Inbred SHR A strain of Rattus norvegicus with elevated blood pressure used as a model for studying hypertension and stroke. Rats, Spontaneously Hypertensive,Rats, SHR,Inbred SHR Rat,Inbred SHR Rats,Rat, Inbred SHR,Rat, SHR,Rat, Spontaneously Hypertensive,SHR Rat,SHR Rat, Inbred,SHR Rats,SHR Rats, Inbred,Spontaneously Hypertensive Rat,Spontaneously Hypertensive Rats
D011919 Rats, Inbred Strains Genetically identical individuals developed from brother and sister matings which have been carried out for twenty or more generations or by parent x offspring matings carried out with certain restrictions. This also includes animals with a long history of closed colony breeding. August Rats,Inbred Rat Strains,Inbred Strain of Rat,Inbred Strain of Rats,Inbred Strains of Rats,Rat, Inbred Strain,August Rat,Inbred Rat Strain,Inbred Strain Rat,Inbred Strain Rats,Inbred Strains Rat,Inbred Strains Rats,Rat Inbred Strain,Rat Inbred Strains,Rat Strain, Inbred,Rat Strains, Inbred,Rat, August,Rat, Inbred Strains,Rats Inbred Strain,Rats Inbred Strains,Rats, August,Rats, Inbred Strain,Strain Rat, Inbred,Strain Rats, Inbred,Strain, Inbred Rat,Strains, Inbred Rat
D001794 Blood Pressure PRESSURE of the BLOOD on the ARTERIES and other BLOOD VESSELS. Systolic Pressure,Diastolic Pressure,Pulse Pressure,Pressure, Blood,Pressure, Diastolic,Pressure, Pulse,Pressure, Systolic,Pressures, Systolic
D002264 Carboxylic Acids Organic compounds containing the carboxy group (-COOH). This group of compounds includes amino acids and fatty acids. Carboxylic acids can be saturated, unsaturated, or aromatic. Carboxylic Acid,Acid, Carboxylic,Acids, Carboxylic
D000806 Angiotensin-Converting Enzyme Inhibitors A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility. ACE Inhibitor,ACE Inhibitors,Angiotensin Converting Enzyme Inhibitor,Angiotensin I-Converting Enzyme Inhibitor,Angiotensin-Converting Enzyme Inhibitor,Kininase II Inhibitor,Kininase II Inhibitors,Angiotensin I-Converting Enzyme Inhibitors,Angiotensin-Converting Enzyme Antagonists,Antagonists, Angiotensin-Converting Enzyme,Antagonists, Kininase II,Inhibitors, ACE,Inhibitors, Angiotensin-Converting Enzyme,Inhibitors, Kininase II,Kininase II Antagonists,Angiotensin Converting Enzyme Antagonists,Angiotensin Converting Enzyme Inhibitors,Angiotensin I Converting Enzyme Inhibitor,Angiotensin I Converting Enzyme Inhibitors,Antagonists, Angiotensin Converting Enzyme,Enzyme Antagonists, Angiotensin-Converting,Enzyme Inhibitor, Angiotensin-Converting,Enzyme Inhibitors, Angiotensin-Converting,II Inhibitor, Kininase,Inhibitor, ACE,Inhibitor, Angiotensin-Converting Enzyme,Inhibitor, Kininase II,Inhibitors, Angiotensin Converting Enzyme
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D051381 Rats The common name for the genus Rattus. Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus

Related Publications

K Hayashi, and K Nunami, and J Kato, and N Yoneda, and M Kubo, and T Ochiai, and R Ishida
Angiotensin converting enzyme inhibitors: 1-glutarylindoline-2-carboxylic acids derivatives.
September 1983, Journal of medicinal chemistry,
K Hayashi, and K Nunami, and J Kato, and N Yoneda, and M Kubo, and T Ochiai, and R Ishida
Design, synthesis and enzyme inhibitory activities of new trifluoromethyl-containing inhibitors for angiotensin converting enzyme.
February 1994, Drug design and discovery,
K Hayashi, and K Nunami, and J Kato, and N Yoneda, and M Kubo, and T Ochiai, and R Ishida
Angiotensin-converting enzyme inhibitors. 2. Perhydroazepin-2-one derivatives.
February 1988, Journal of medicinal chemistry,
K Hayashi, and K Nunami, and J Kato, and N Yoneda, and M Kubo, and T Ochiai, and R Ishida
Synthesis and angiotensin converting enzyme inhibitory activity of N-carboxymethyldipeptides with omega-(4-piperidyl)alkyl group.
April 1990, Arzneimittel-Forschung,
K Hayashi, and K Nunami, and J Kato, and N Yoneda, and M Kubo, and T Ochiai, and R Ishida
Angiotensin-converting enzyme inhibitors. 9. Novel [[N-(1-carboxy-3-phenylpropyl)amino]acyl]glycine derivatives with diuretic activity.
June 1990, Journal of medicinal chemistry,
K Hayashi, and K Nunami, and J Kato, and N Yoneda, and M Kubo, and T Ochiai, and R Ishida
Synthesis, Antiviral and Cytotoxic Activities of 2-(2-Phenyl carboxylic acid)-3-Phenylquinazolin -4(3H)-one Derivatives.
November 2010, Indian journal of pharmaceutical sciences,
K Hayashi, and K Nunami, and J Kato, and N Yoneda, and M Kubo, and T Ochiai, and R Ishida
Novel 2-oxoimidazolidine-4-carboxylic acid derivatives as hepatitis C virus NS3-4A serine protease inhibitors: synthesis, activity, and X-ray crystal structure of an enzyme inhibitor complex.
December 2004, Bioorganic & medicinal chemistry letters,
K Hayashi, and K Nunami, and J Kato, and N Yoneda, and M Kubo, and T Ochiai, and R Ishida
[Synthesis of some derivatives of 1-alkyl-4-acyl-4-phenylpiperidines. I. Synthesis of 4-acyl-4-phenylpiperidines].
January 1969, Acta poloniae pharmaceutica,
K Hayashi, and K Nunami, and J Kato, and N Yoneda, and M Kubo, and T Ochiai, and R Ishida
[Synthesis of some 1-(3-(dialkylamino)-propyl)-4-acyl-4-phenyl-piperidines. 3. Derivatives of 1-alkyl-4-4-acetyl-4-phenylpiperidine and 1-alkyl-4-phenyl-4-propionylpiperidine].
January 1971, Acta poloniae pharmaceutica,
K Hayashi, and K Nunami, and J Kato, and N Yoneda, and M Kubo, and T Ochiai, and R Ishida
Synthesis and angiotensin converting enzyme-inhibitory activity of N-[(1S)-1-carboxy-5-(4-piperidyl)pentyl]-L-alanine derivatives.
March 1994, Chemical & pharmaceutical bulletin,
Copied contents to your clipboard!