232-85-9Relevant articles and documents
Mannich bases of 3H-pyrrolo[3,2-f]quinoline having vasorelaxing activity
Ferlin, Maria Grazia,Chiarelotto, Gianfranco,Antonucci, Francesca,Caparrotta, Laura,Froldi, Guglielmina
, p. 427 - 434 (2002)
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 μM 5-hydroxytryptamine (5-HT), 3 μM 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 β-receptor antagonist, and ketanserin, a 5-HT2A-receptor antagonist, was checked. In the presence of phenylephrine, the vasorelaxing effect of Ia was not affected by these inhibitors.
A new ring-forming methodology for the synthesis of bioactive pyrroloquinoline derivatives
Vlachou, Margarita,Tsotinis, Andrew,Kelland, Lloyd R.,Thurston, David E.
, p. 129 - 133 (2007/10/03)
A new, efficient, two-step method for the synthesis of bioactive pyrroloquinolines is described. Readily available nitroquinolines, bearing the nitro moiety in the carbocyclic ring, are treated with 4-chlorophenoxyacetonitrile in the presence of potassium tert-butoxide/THF to give the analogous vicarious nucleophilic substitution products (5, 8 and 11). These, in turn, are subjected to catalytic hydrogenation to produce 1H-pyrrolo[2,3-f]quinoline (6), 3H-pyrrolo[3,2-f]quinoline (9) and 1H-pyrrolo[3,2-h]quinoline (12) in good yields and relatively short reaction times. The differential activity of two N-alkylated 1H-pyrrolo[2,3-f]quinolines (1) in cisplatin resistant cell lines compared to the corresponding parent lines suggests that these might be useful leads for developing agents for use in drug resistant diseases.
