Mannich bases of 3H-pyrrolo[3,2-f]quinoline having vasorelaxing activity.
Mannich bases obtained by aminoalkylation of 3H-pyrrolo[3,2-f]quinoline were designed and prepared as potential vasorelaxing agents. Compounds Ia-Va were characterised by IR, 1H-NMR, mass spectral data and elemental analysis; IIb,c-Vb,c were also confirmed by 1H-NMR spectra of reaction mixtures. To estimate their vascular activity, prototypes 1-(N,N-dimethylaminomethyl)- (Ia) and 1-(4-phenyl-piperazin-1-ylmethyl)- (IVa) 3H-pyrrolo[3,2-f]quinoline derivatives were studied in rat-tail arteries. In tissues precontracted with 0.5 microM 5-hydroxytryptamine (5-HT), 3 microM phenylephrine or 80 mM KCl, Ia and IVa showed endothelium-independent relaxing action. In a preliminary study on the cellular mechanisms of Ia, the influence of propranolol, a beta-receptor antagonist, and ketanserin, a 5-HT(2A)-receptor antagonist, was checked. In the presence of phenylephrine, the vasorelaxing effect of Ia was not affected by these inhibitors.
Ferlin
Maria Grazia
MG
Department of Pharmaceutical Sciences, University of Padova, Via Marzolo 5, Italy.
Chiarelotto
Gianfranco
G
Antonucci
Francesca
F
Caparrotta
Laura
L
Froldi
Guglielmina
G
D000818:Animals; D001158:Arteries / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008352:Mannich Bases; D009131:Muscle, Smooth, Vascular / Q000187:drug effects; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D017208:Rats, Wistar; D013623:Tail / Q000098:blood supply; D014664:Vasodilation / Q000187:drug effects*; D014665:Vasodilator Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
C470129:1-(4-phenylpiperazin-1-ylmethyl)-3H-pyrrolo(3,2-f)quinoline; C470128:1-(N,N-dimethylaminomethyl)-3H-pyrrolo(3,2-f)-quinoline; D008352:Mannich Bases; D010879:Piperazines; D011758:Pyrroles; D011804:Quinolines; D014665:Vasodilator Agents