The biological activity of two symmetric amine derivatives of the cis-syn-cis triquinane system.
N-benzyl-3,11-azatricyclo[6.3.0.0]undecane and N-octyl-3,11-azatricyclo[6.3.0.0]undecane, two triquinane compounds containing an endocyclic nitrogen atom and differing side-chains, were synthesized by thermal 2 + 2 cycloreversion from the symmetric cage compound pentacyclo[5.4.0.0.0.0]undecane-8,11-dione. The conformation of the cyclic system showed close similarity with the conformation of the hydrate of 4-methyltricyclo[6.3.0.0]undeca-3,11-dione. Both N-benzyl-3,11-azatricyclo[6.3.0.0]undecane and N-octyl-3,11-azatricyclo[6.3.0.0]undecane showed similar suppressant activity on the Ca2+ action potential of guinea-pig papillary muscle--the benzyl (aromatic) derivative fully suppressed the action potential (AP) whilst the aliphatic (octyl) derivative suppressed the AP to about 50% at the same dosages. Similarly, both these compounds (irreversibly) suppressed the chronotropy of spontaneously contracting guinea-pig atria by approximately 30% at concentrations of 1 x 10(-5) M or more.
Liebenberg
W
W
Department of Pharmaceutical Chemistry, Potchefstroom University for Christian Higher Education, South Africa.
Van Rooyen
P H
PH
Van Der Schyf
C J
CJ
D000200:Action Potentials / Q000187:drug effects; D000818:Animals; D002118:Calcium / Q000502:physiology; D002316:Cardiotonic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004594:Electrophysiology; D006168:Guinea Pigs; D006339:Heart Rate / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008968:Molecular Conformation; D009131:Muscle, Smooth, Vascular / Q000187:drug effects; D009200:Myocardial Contraction / Q000187:drug effects; D010210:Papillary Muscles / Q000187:drug effects
D002316:Cardiotonic Agents; D006571:Heterocyclic Compounds; C103010:N-benzyl-3,11-azatricyclo(6.3.0.0(2,6))undecane; C103011:N-octyl-3,11-azatricyclo(6.3.0.0(2,6))undecane; D002118:Calcium