6533b7d8fe1ef96bd126b77b

RESEARCH PRODUCT

Synthesis, Optical Properties, and DNA Interaction of New Diquats Based on Triazolopyridines and Triazoloquinolines

Ramón J. ZaragozáBelén AbarcaM. José AurellRafael BallesterosEnrique García-españaRafael Ballesteros-garridoClaudia GiarratanoPedro J. Llabres-campanerLluis Guijarro

subject

Models MolecularMagnetic Resonance SpectroscopyStatic ElectricityIntercalation (chemistry)Molecular Conformation010402 general chemistryPhotochemistry01 natural sciencesMedicinal chemistryCatalysischemistry.chemical_compoundUltraviolet visible spectroscopyPyridineDiquatAlkylchemistry.chemical_classificationAlkane010405 organic chemistryQuinolinium CompoundsOrganic ChemistryQuinolineStereoisomerismDNAGeneral ChemistryTriazolesFluorescenceIntercalating Agents0104 chemical sciencesPyrimidineschemistrySpectrophotometryThermodynamicsEnantiomer

description

New diquat derivatives based on [1,2,3]triazolo[1,5-a]pyridine and [1,2,3]triazolo[1,5-a]quinoline have been synthesized in excellent yields. To evaluate the effect of the alkyl bridge length, ethane and propane dibromo alkane substrates were used for their synthesis. Theoretical calculations predicted a very small energetic barrier between the two possible enantiomers P (Ra ) and M (Sa ), which makes them very difficult to resolve. Thermal denaturation studies, UV/Visible spectroscopy, and fluorescence titrations with ct-DNA evidenced the intercalation of the quinoline derivatives in DNA.

https://doi.org/10.1002/chem.201701618