200491-51-6Relevant articles and documents
New 2-(aryl/heteroaryl)-6-(morpholin-4-yl/pyrrolidin-1-yl)-(4-trifluoromethyl)quinolines: Synthesis: via Buchwald-Hartwig amination, photophysics, and biomolecular binding properties
Bonacorso, Helio G.,Rodrigues, Melissa B.,Iglesias, Bernardo A.,Da Silveira, Carolina H.,Feitosa, Sarah C.,Rosa, Wilian C.,Martins, Marcos A. P.,Frizzo, Clarissa P.,Zanatta, Nilo
, p. 10024 - 10035 (2018/06/18)
This work reports a successful synthesis of two new series of 2-(aryl/heteroaryl)-6-(morpholin-4-yl/pyrrolidin-1-yl)-(4-trifluoromethyl)quinolines via the Buchwald-Hartwig amination, at 60-88% yields, starting from 2-(aryl/heteroaryl)-6-bromo-4-trifluoromethyl-quinolines and heteroarylamines (morpholine and pyrrolidine). The 6-bromoquinoline precursors were obtained from an easy intramolecular cyclization reaction of (Z)-4-((4-bromophenyl)amino)-1,1,1-trifluoro-but-3-en-2-ones, which were previously prepared through the reaction of 4-methoxy-(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones with 4-bromoaniline. Photophysical analyses indicated intraligand and charge-transfer type transitions, in agreement with the aromatic structures of the heterocycle moieties. In the case of ct-DNA titrations (via the absorption and emission method), morpholinyl- and pyrrolydinyl-substituted quinolines had strong interactions with ct-DNA, which could be attributed to π-stacking and/or hydrogen-bonding interactions.
