A new modification of the Friedländer synthesis. A simple route to 2-aminoquinoline-3-carboxylic acid and its derivatives

Ukhin, L. Yu.; Belov, E. G.

doi:10.1007/s11172-008-0065-0

Cited by 6 publications

(2 citation statements)

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“…2-Aminobenzaldehyde is not stable, [28] and thus, it was generated in situ by reduction of 2-nitrobenzaldehyde. [29] An overall yield of 75 % was obtained for the two-step, one-pot process.…”

Section: Resultsmentioning

confidence: 99%

“…BisQ was prepared by following procedure described in the literature [10] based on a double Friedländer condensation between two equivalents of 2-aminobenzaldehyde and 2,6acetylpyridine (Scheme 3). 2-Aminobenzaldehyde is not stable, [28] and thus, it was generated in situ by reduction of 2-nitrobenzaldehyde. [29] An overall yield of 75 % was obtained for the two-step, one-pot process.…”

Section: Resultsmentioning

confidence: 99%

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Tridentate N‐Donor Palladium(II) Complexes as Efficient Coordinating Quadruplex DNA Binders

Largy

Hamon

Rosu

et al. 2011

Chemistry A European J

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Fifteen complexes of palladium, platinum, and copper, featuring five different N-donor tridentate (terpyridine-like) ligands, were prepared with the aim of testing their G-quadruplex-DNA binding properties. The fluorescence resonance energy transfer melting assay indicated a striking positive effect of palladium on G-quadruplex DNA stabilization compared with platinum and copper, as well as an influence of the structure of the organic ligand. Putative binding modes (noncoordinative π stacking and base coordination) of palladium and platinum complexes were investigated by ESI-MS and UV/Vis spectroscopy experiments, which all revealed a greater ability of palladium complexes to coordinate DNA bases. In contrast, platinum compounds tend to predominantly bind to quadruplex DNA in their aqua form by noncoordinative interactions. Remarkably, complexes of [Pd(ttpy)] and [Pd(tMebip)] (ttpy = tolylterpyridine, tMebip = 2,2'-(4-p-tolylpyridine-2,6-diyl)bis(1-methyl-1H-benzo[d]imidazole)) coordinate efficiently G-quadruplex structures at room temperature in less than 1 h, and are more efficient than their platinum counterparts for inhibiting the growth of cancer cells. Altogether, these results demonstrate that both the affinity for G-quadruplex DNA and the binding mode of metal complexes can be modulated by modifying either the metal or the organic ligand.

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Section: Resultsmentioning

confidence: 99%