Synthesis of hexahydro-1H-pyrido[3,2-c]azepines as hypotensive agents of expected calcium-channel blocking activity

被引：6

作者：

El-Sadek, Mohamed E. ^{[1
]}

Aboukull, Mansour ^{[1
]}

El-Sabbagh, Osama I. ^{[1
]}

Shallal, Hassan M. ^{[1
]}

机构：

[1] Zagazig Univ, Fac Pharm, Dept Med Chem, Zagazig, Egypt

来源：

MONATSHEFTE FUR CHEMIE | 2007年 / 138卷 / 03期

关键词：

hexahydroquinolines; pyrido[3,2-c]azepines; hypotensive activity; nefidipine;

D O I：

10.1007/s00706-007-0586-5

中图分类号：

O6 [化学];

学科分类号：

0703 [化学];

摘要：

Michael addition reaction of 3-(4-fluorophenylamino)-2-cyclohexenone and its 5,5-dimethyl derivative to the acrylonitrile derivatives afforded the novel hexahydroquinolines. The target hexahydro-1H-pyrido[3,2-c]azepine derivatives were obtained via ring enlargement of the corresponding hexahydroquinolines under Schmedt conditions. Some novel pyrido[3,2-c]azepines showed hypotensive activity in vivo on normotensive anaesthetized male adult albino rats and their effects on the ventricular contraction and auricular rate of isolated rabbit hearts using Langendorff's method and nefidipine as a reference drug were studied. Compounds 29 and 36 which bear some structural similarities to nefidipine exhibited the highest hypotensive activity and negative inotropic as well as chronotropic activities.

引用

页码：219 / 225

页数：7

共 27 条

[1]

ALASHMAWI M, 1991, B FAC PHARM CAIRO, V29, P9

[2]

ALBERT D, 1989, J MED CHEM, V32, P2178

[3]

ALMANGE L, 1969, CHEM REV, V69, P609

[4]

[Anonymous], [No title captured], Patent No. 0002861

[5]

SYNTHESIS AND TRANSFORMATIONS OF SOME QUINOLINES AND 1H-PYRIDO[3,2-C]AZEPINES CONTAINING AMINO-ACID UNITS [J].

ANZIC, B ;

KOCEVAR, M ;

POLANC, S .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (06) :1305-1309

[6]

Dihydropyridines from the first to the fourth generation: Better efficacy and safety [J].

Aouam, K ;

Berdeaux, A .

THERAPIE, 2003, 58 (04) :333-339

[7]

ARMITAGE P, 1974, STATISTICAL METHODS, P116

[8]

SIMPLE METHOD FOR RECORDING LEFT-VENTRICULAR PRESSURE DP-DT AND HEART-RATE IN THE CONSCIOUS CAT [J].

BURDEN, DT ;

BLABER, LC ;

NATOFF, IL .

PHARMACOLOGY & THERAPEUTICS, 1979, 5 (1-3) :99-102

[9]

BURN JH, 1952, PRACTICAL PHARMACOLO, P25

[10]

CARSON BB, 1928, J AM CHEM SOC, V50, P2825

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