105199-23-3Relevant academic research and scientific papers
Pyrroloquinoline scaffold-based 5-HT6R ligands: Synthesis, quantum chemical and molecular dynamic studies, and influence of nitrogen atom position in the scaffold on affinity
Grychowska, Katarzyna,Kurczab, Rafa?,?liwa, Pawe?,Sata?a, Grzegorz,Dubiel, Krzysztof,Mat?oka, Miko?aj,Moszczyński-P?tkowski, Rafa?,Pieczykolan, Jerzy,Bojarski, Andrzej J.,Zajdel, Pawe?
, p. 3588 - 3595 (2018)
Based on pyrroloquinoline scaffold bearing 5-HT2C agonists, a series of arylsulfonamide derivatives of 1H-pyrrolo[2,3-f]quinoline and 1H-pyrrolo[3,2-h]quinoline, substituted at position 3 with tetrahydropyridine, were synthesized and evaluated in vitro for their affinity for 5-HT6 receptors. A structure–activity relationship study showed that the 1H-pyrrolo[3,2-h]quinoline scaffold was more favorable for 5-HT6R binding than the 1H-pyrrolo[2,3-f]quinoline one, suggesting dependence upon the type of condensation of the pyrrole and quinoline rings. As revealed by quantum-chemical calculations and molecular dynamic studies, position of the quinoline nitrogen atom in the planar pyrroloquinoline skeleton might affect the spatial orientation of the arylsulfonyl fragment, as a result of structure stabilization by internal hydrogen bonds.
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.
Vicarious Nucleophilic Substitution in Nitroquinolines
Makosza, Mieczyslaw,Kinowski, Andrzej,Danikiewicz, Witold,Mudryk, Boguslaw
, p. 69 - 77 (2007/10/02)
5-Nitro-, 6-nitro-, and 8-nitroquinoline react with the carbanions of chloromethyl phenyl sulfone, chloro-N,N-dimethylmethanesulfonamide and substituted acetonitriles XCH2CN (X=OPh, SPh, Cl) giving products of the vicarious nucleophilic substitution of hy
