Novel Schiff Bases Based on the Quinolinone Skeleton: Syntheses, X-ray Structures and Fluorescent Properties

Molecules

Zdeněk Trávníპk¹  Roman Buchtík² 

[1] Regional Centre of Advanced Technologies and Materials, Department of Inorganic Chemistry, Faculty of Science, Palacký University, 17 listopadu 12, CZ-77146 Olomouc, Czech Republic;

关键词: 2-phenyl-3-amino-4(1H)-quinolinone;    Schiff base;    fluorescence;    in vitro cytotoxicity;    X-ray structures;   

DOI  :  10.3390/molecules190913509

来源: mdpi

【 摘 要 】

A series of a new type of Schiff bases 1–7, derived from 2-phenyl-3-amino-4(1H)-quinolinone and R-salicyladehyde derivatives wherein R = 3-hydroxy (1), 3,4-dihydroxy (2), 3-methoxy (3), 3-carboxy (4), 3-allyl (5), 5-chloro (6), and 5-nitro (7), was synthesized and structurally characterized. Each of the molecules 1, 3 and 7 consists of three planar moieties (i.e., a quinolinone and two phenyl rings), which are mutually oriented differently depending on the appropriate substituent R and the extent of non-covalent contacts stabilizing the crystal structures. The compounds were studied for their fluorescence properties, where compound 6 yielded the strongest intensity both in the solid phase and in 100 μM ethanol solution with a quantum yield of φ = 3.6% as compared to quinine sulfate used as a standard. The in vitro cytotoxicity of these compounds was tested against the human osteosarcoma (HOS) and breast adenocarcinoma (MCF7) cell lines, revealing no activity up to the concentration of 50 µM.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.