Ullmann-type copper-catalyzed coupling amination, photophysical and DNA/HSA-binding properties of new 4-(trifluoromethyl)quinoline derivatives

被引：13

作者：

Rodrigues, Melissa B. ^{[1
]}

Feitosa, Sarah C. ^{[1
]}

Wiethan, Carson W. ^{[1
]}

Rosa, Wilian C. ^{[1
]}

da Silveira, Carolina H. ^{[2
]}

Pagliari, Anderson B. ^{[1
]}

Martins, Marcos A. P. ^{[1
]}

Zanatta, Nilo ^{[1
]}

Iglesias, Bernardo A. ^{[2
]}

Bonacorso, Helio G. ^{[1
]}

机构：

[1] Univ Fed Santa Maria, Dept Quim, Nucleo Quim Heterociclos NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil

[2] Univ Fed Santa Maria, Dept Quim, Lab Bioinorgan & Mat Porfirin, BR-97105900 Santa Maria, RS, Brazil

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2019年 / 221卷

关键词：

Ullmann cross-coupling; Quinolines; Indoles; Photophysical properties; DNA-binding; HSA-binding; REGIOSELECTIVE SYNTHESIS; SERUM-ALBUMIN; ENOL ETHERS; FLUORESCENCE; ARYLATION; ACYLATION; DOCKING; SERIES; ACIDS; NMR;

D O I：

10.1016/j.jfluchem.2019.04.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

This paper describes the synthesis of a novel series of 2-aryl-6-(1H-indol-1-yl)-4-(trifluoromethyl)quinolines, in which aryl = C6H5, 4-CH3C6H4, 4-FC6H4, 4-CF3C6H4 and heteroaryl = 2-thienyl, by an Ullmann-type cooper-catalyzed amination cross-coupling reaction. Photophysical properties of indolyl-quinolines were investigated using absorption and emission analysis. The emission fluorescence analysis showed a blue to cyan region emission in the 400-650 nm range. Large Stokes shifts values were observed for all new quinolines and attributed to the ICT state and to the electron-substituent properties. The ability to generate O-1(2) species after being exposed to white light and biomolecule-binding DNA / HSA properties were also investigated.

引用

页码：84 / 90

页数：7

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