Journal of Medicinal Chemistry p. 1496 - 1504 (1990)
Update date:2022-08-04
Topics:
Reiffen
Eberlein
Muller
Psiorz
Noll
Heider
Lillie
Kobinger
Luger
Structural modification of the calcium-antagonist verapamil (1) by replacement of the lipophilic α-isopropylacetonitrile moiety by various heterocyclic ring systems has led to a new class of cardiovascular compounds which are characterized by a specific bradycardic activity. These agents reduce heart rate without binding to classical calcium channels or β-adrenoceptors, interacting instead specifically with structures at the sino atrial node. Therefore they have also been termed sinus node inhibition. The prototype falipamil (2) has been submitted to furthr optimization mainly hy manipulation of the phthalimidine moiety. This has resultd in a secod generation of specific bradycardic agents with increased potency and selectively and prolonged duration of action represented by the benzazepinone-derivative UL-FS 49 (4). Structure-activity relationships within this novel class of compounds have revealed a marked dependence of activity on the substitution pattern of the aromatic rings, the nature of the central nitrogen atom, and the length of the connecting alkyl chains. The crucial role of the benzazepione ring for bradycardic activity can be best explained by its special impact on the overall molecular conformation.
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