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alpha-[(3S)-3-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2-oxo-6 or 7-phenylperhydroazepin-1-yl]acetic acids (monoester monoacids) and their dicarboxylic acids were synthesized, and their angiotensin-converting enzyme (ACE) inhibitory activities were evaluated. The dicarboxylic acids having phenyl substituents at the 6R, 6S, and 7S positions on the azepinone ring showed potent inhibition in vitro. The corresponding monoester monoacids, when administered orally, suppressed the pressor response to angiotensin I administered intravenously. The monoester monoacids having the phenyl substituent at the 6-position showed a longer duration of action than one having the substituent at the 7-position. The structure-activity relationship was studied on the basis of the conformational energy calculation.
H Yanagisawa, and
S Ishihara, and
A Ando, and
T Kanazaki, and
S Miyamoto, and
H Koike, and
Y Iijima, and
K Oizumi, and
Y Matsushita, and
T Hata
November 1985,
Journal of medicinal chemistry,
H Yanagisawa, and
S Ishihara, and
A Ando, and
T Kanazaki, and
S Miyamoto, and
H Koike, and
Y Iijima, and
K Oizumi, and
Y Matsushita, and
T Hata
September 1983,
Journal of medicinal chemistry,
H Yanagisawa, and
S Ishihara, and
A Ando, and
T Kanazaki, and
S Miyamoto, and
H Koike, and
Y Iijima, and
K Oizumi, and
Y Matsushita, and
T Hata
October 1985,
Journal of medicinal chemistry,
H Yanagisawa, and
S Ishihara, and
A Ando, and
T Kanazaki, and
S Miyamoto, and
H Koike, and
Y Iijima, and
K Oizumi, and
Y Matsushita, and
T Hata
April 1990,
American journal of hypertension,
H Yanagisawa, and
S Ishihara, and
A Ando, and
T Kanazaki, and
S Miyamoto, and
H Koike, and
Y Iijima, and
K Oizumi, and
Y Matsushita, and
T Hata
January 1995,
Journal de pharmacie de Belgique,
H Yanagisawa, and
S Ishihara, and
A Ando, and
T Kanazaki, and
S Miyamoto, and
H Koike, and
Y Iijima, and
K Oizumi, and
Y Matsushita, and
T Hata
September 1987,
The Medical clinics of North America,
H Yanagisawa, and
S Ishihara, and
A Ando, and
T Kanazaki, and
S Miyamoto, and
H Koike, and
Y Iijima, and
K Oizumi, and
Y Matsushita, and
T Hata
May 1992,
AACN clinical issues in critical care nursing,
H Yanagisawa, and
S Ishihara, and
A Ando, and
T Kanazaki, and
S Miyamoto, and
H Koike, and
Y Iijima, and
K Oizumi, and
Y Matsushita, and
T Hata
July 2006,
Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti,
H Yanagisawa, and
S Ishihara, and
A Ando, and
T Kanazaki, and
S Miyamoto, and
H Koike, and
Y Iijima, and
K Oizumi, and
Y Matsushita, and
T Hata
September 2011,
Journal of clinical hypertension (Greenwich, Conn.),
H Yanagisawa, and
S Ishihara, and
A Ando, and
T Kanazaki, and
S Miyamoto, and
H Koike, and
Y Iijima, and
K Oizumi, and
Y Matsushita, and
T Hata
November 1980,
American family physician,
