An Interesting Synthetic Pathway to Some Quinolin-4(1H)ones: Phenacylanthranilates Rearrangement – Limits and Scopes

Soural, Miroslav; Hradil, Pavel; Křupková, Soňa; Hlaváč, Jan

doi:10.2174/157019312804699483

Cited by 13 publications

(11 citation statements)

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“…https://doi.org/10.1016/j.dyepig.2018.10.027 Received 14 September 2018; Received in revised form 16 October 2018; Accepted 17 October 2018 Particularly, quinolin-4(1H)-one scaffold containing compounds represent extremely large group of organic substances that have been studied very extensively for many reasons [11]. Numerous dedicated articles can be found describing preparation and biological properties of variously substituted quinolin-4(1H)-ones.…”

Section: Introductionmentioning

confidence: 99%

3-Hydroxykynurenic acid: Physicochemical properties and fluorescence labeling

et al. 2019

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Quinoline is one of the most important heterocyclic systems in life sciences. Some derivatives are normal metabolites, and others are used as antibacterial, antimalarial, and anticancer agents. In this work, we describe the synthesis, physicochemical properties, and fluorescence features of a new 4-quinolinone fluorophore, 3-hydroxykynurenic acid (3-HOKA). 3-HOKA was obtained by alkoxide-induced rearrangement of ethyl isatinacetate followed by acidification and then alkaline hydrolysis. The fluorescent compound was characterized by NMR, MS, IR, and UV-Vis spectra. 3-HOKA can exist under a keto-enol equilibrium, but the 4-quinolinone form is the predominant tautomer. In PBS (pH = 7.4), the anionic keto form of 3-HOKA showed a maximum absorption at 368 nm, a fluorescence peak at 474 nm, and a fluorescence quantum yield (Φ F): 0.73. 3-HOKA is photostable and is a moderately weak oxygen generator. Viability assays on HeLa cells indicated that 3-HOKA did not induce significative cytotoxic effects. Under UV excitation, a bright blue fluorescence was selectively found in a singular body within the cytoplasm, a labeling pattern that suggests the possible localization of the probe in the centriole or related structures. Therefore, this novel fluorophore represents a promising prototype compound owing to its biocompatibility and potential biological applications.

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Section: Introductionmentioning

confidence: 99%

3-Hydroxykynurenic acid: Physicochemical properties and fluorescence labeling

et al. 2019

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“…Acid-mediated rearrangement of phenacyl anthranilates furnishes 3-hydroxyquinolin-4(1H)-ones in high yields. 30 In 2007, this synthetic strategy was introduced on solid-phase (Scheme 27). 31 Polymer-supported amines 129 were acylated with 2-aminoterephthalic acid methyl ester followed by saponification of the methyl ester group to give carboxylic acids 131.…”

Section: Quinolines: Path Bmentioning

confidence: 99%

Solid-Phase Synthesis of Heterocycles with α-Haloketones as the Key Building Blocks

Fülöpová

Soural

2016

Synthesis

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This short review summarizes the use of α-haloketones in the preparation of various heterocycles with the application of solidphase synthesis. A literature survey revealed that eighteen different five-to-seven membered scaffolds are accessible, including condensed heterocycles and bisheterocycles. 22 Conclusion Key words α-haloketones, heterocycles, rearrangement, solid-phase synthesis, cyclization Miroslav Soural (left) was born in Olomouc, Czech Republic, in 1978. He studied chemistry at Palacky University, Olomouc, where he also received his Ph.D. in organic chemistry (in 2006). After his postdoctoral fellowship at the University of Notre Dame (USA), he was appointed Associated Professor at Palacky University, Olomouc. From 2012 he has held the position of Senior Researcher at the Institute of Molecular and Translational Medicine. His field of interest is the development of strategies for the solid-phase synthesis of various pharmacologically promising substances with the emphasis on heterocyclic chemistry. Veronika Fülöpová (right) was born in Opava, Czech Republic, in 1985. During her graduate studies at Palacky University, Olomouc (Czech Republic) she became an investigator on several student grant projects regarding the solid-phase synthesis of novel heterocyclic compounds. After defending her Ph.D. thesis devoted to nitrobenzenesulfonamide chemistry, she received her Ph.D. degree in 2015 from the same university. Currently, she is working as a researcher at the Institute of Molecular and Translational Medicine in Olomouc, and the main area of her interest is solution-/solid-phase synthesis of nitrogenous heterocycles with potential biological activity.

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“…Quinolin-4(1H)-ones are ubiquitously present in numerous natural products and drugs, representing an important class of privileged structures in medicinal chemistry [1][2][3][4][5], such as antibiotics norfloxacin and gatifloxacin, a HIV integrase inhibitor, elvitegravir, and a modulator of ATP-binding cassette transporters, lvacaftor (Figure 1). Therefore, the development of highly efficient protocols both in transition-metal-catalyzed C-H activation and photocatalytic methods for the construction of such N-heterocyclic scaffolds is an extremely hot issue in modern organic chemistry [6][7][8][9][10][11][12]. However, the existing methodologies usually require elaborate-to-access starting materials, multiple steps, or harsh reaction conditions, failing to implement a wide range of applications.…”

Section: Introductionmentioning

confidence: 99%