Liebenberg W, Van Rooyen P H, Van Der Schyf C J
Department of Pharmaceutical Chemistry, Potchefstroom University for Christian Higher Education, South Africa.
Pharmazie. 1996 Jan;51(1):20-4.
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.
N-苄基-3,11-氮杂三环[6.3.0.0]十一烷和N-辛基-3,11-氮杂三环[6.3.0.0]十一烷是两种含有环内氮原子且侧链不同的三环癸烷化合物，它们由对称笼状化合物五环[5.4.0.0.0.0]十一烷-8,11-二酮通过热2 + 2环化反转反应合成。环状体系的构象与4-甲基三环[6.3.0.0]十一烷-3,11-二酮水合物的构象非常相似。N-苄基-3,11-氮杂三环[6.3.0.0]十一烷和N-辛基-3,11-氮杂三环[6.3.0.0]十一烷对豚鼠乳头肌的Ca2+动作电位均表现出相似的抑制活性——苄基（芳香族）衍生物完全抑制动作电位（AP），而脂肪族（辛基）衍生物在相同剂量下将AP抑制约50%。同样，在浓度为1×10(-5) M或更高时，这两种化合物（不可逆地）使自发收缩的豚鼠心房的变时性抑制约30%。
