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Molecules 2014, 19(9), 13509-13525; doi:10.3390/molecules190913509

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

Regional Centre of Advanced Technologies and Materials, Department of Inorganic Chemistry, Faculty of Science, Palacký University, 17 listopadu 12, CZ-77146 Olomouc, Czech Republic
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Received: 1 July 2014 / Revised: 12 August 2014 / Accepted: 25 August 2014 / Published: 1 September 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

A series of a new type of Schiff bases 17, 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. View Full-Text
Keywords: 2-phenyl-3-amino-4(1H)-quinolinone; Schiff base; fluorescence; in vitro cytotoxicity; X-ray structures 2-phenyl-3-amino-4(1H)-quinolinone; Schiff base; fluorescence; in vitro cytotoxicity; X-ray structures
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Trávníček, Z.; Buchtík, R.; Nemec, I. Novel Schiff Bases Based on the Quinolinone Skeleton: Syntheses, X-ray Structures and Fluorescent Properties. Molecules 2014, 19, 13509-13525.

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