Cardiotonic agents. 6. Synthesis and inotropic activity of 2,4-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-3H-pyrazol-3-ones: ring-contracted analogs of imazodan (CI-914)

A series of 2,4-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-3H-pyrazol-3-ones was synthesized and evaluated for positive inotropic activity. Only compounds with two small alkyl groups at C-4 showed significant activity. The structure-activity relationships for optimal inotropic activity are presented and...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1987-10, Vol.30 (10), p.1724-1728
Main Authors: Sircar, Ila, Morrison, Glenn C, Burke, Sandra E, Skeean, Richard, Weishaar, Ronald E
Format: Article
Language:English
Subjects:
Animals
Cardiotonic Agents - chemical synthesis
Cardiotonic Agents - pharmacology
Dogs
Guinea Pigs
Myocardial Contraction - drug effects
Phosphodiesterase Inhibitors - chemical synthesis
Phosphodiesterase Inhibitors - pharmacology
Pyridazines - chemical synthesis
Pyridazines - pharmacology
Structure-Activity Relationship
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Summary:A series of 2,4-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-3H-pyrazol-3-ones was synthesized and evaluated for positive inotropic activity. Only compounds with two small alkyl groups at C-4 showed significant activity. The structure-activity relationships for optimal inotropic activity are presented and compared with those of the 4,5-dihydro-3(2H)-pyridazinone series. The phosphodiesterase inhibitory activity is also reported and correlated with the substitution pattern at C-4 in the pyrazolone ring.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00393a007