Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

Kimmel, Roman; Kafka, Stanislav; Košmrlj, Janez

doi:10.1016/j.carres.2010.01.023

Cited by 14 publications

(15 citation statements)

References 69 publications

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“…To obtain the desired ligand 3a, diethanolamine 4 and galactose 1a were protected with tert-butyloxycarbonyl group as described in the literature [20,22], affording 5 and 7 (Scheme 1), respectively, as proved by NMR spectra (Figures S4-S19 at Supplementary Materials). Koenigs-Knorr conditions between 7 and 5, using silver sulphate as a promoter, afforded 9 (S20-S33) [20,[23][24][25]. More information about other promoters is presented at Supplementary Materials.…”

Section: Synthesis and Characterization Of Ligand 3a And Ligand 3a-comentioning

confidence: 99%

Development of Novel Galactosylated PLGA Nanoparticles for Hepatocyte Targeting Using Molecular Modelling

et al. 2020

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Doxorubicin-loaded PLGA nanoparticles conjugated with a new galactose-based ligand for the specific recognition by human hepatoma cellular carcinoma cells (Hep G2) were successfully produced. The new targeting compound was selected using molecular docking combined with quantum chemical calculations for modelling and comparing molecular interactions among the H1 subunit of the asialoglycoprotein receptor containing the carbohydrate recognition domain and the ligand. The ligand, bis(1-O-ethyl-β-D-galactopyranosyl)amine, was synthetized, characterized, and subsequently linked to PLGA. Unloaded (PLGA-di-GAL NP) and doxorubicin-loaded (DOX-PLGA-di-GAL NP) nanoparticles were prepared using an emulsion method and characterized. The produced DOX-PLGA-di-GAL NP are spherical in shape with a size of 258 ± 47 nm, a zeta potential of −62.3 mV, and a drug encapsulation efficiency of 83%. The in vitro drug release results obtained show a three-phase release profile. In vitro cell studies confirmed the interaction between Hep G2 cells and PLGA-di-GAL NP. Cell cytotoxicity tests showed that unloaded NP are nontoxic and that DOX-PLGA-di-GAL NP caused a decrease of around 80% in cellular viability. The strategy used in this work to design new targeting compounds represents a promising tool to develop effective hepatocyte targeting drug delivery systems and can be applied to other tissues/organs. Scheme 1. Synthetic strategy to prepare ligand 3a and PLGA-di-GAL, 10. Promoter = Ag2CO3 or Ag2SO4; catalyst = montmorillonite K10 or methanesulfonic acid.

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Section: Synthesis and Characterization Of Ligand 3a And Ligand 3a-comentioning

confidence: 99%

Development of Novel Galactosylated PLGA Nanoparticles for Hepatocyte Targeting Using Molecular Modelling

et al. 2020

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“…Although N -alkylation of the lactam group usually takes place preferentially in quinoline-2,4(1 H ,3 H )-diones [10], the competitive O -alkylation has been documented in similar systems [19]. The N1 position of thus introduced propargyl group in 7 was confirmed by 2D NMR spectroscopy in particular by the presence of the long-range correlations between the propargyl methylene protons and carbon atoms C-8a and C-2 in the 1 H- 13 C HMBC spectra (in 7a , c , d ) as well as N1 nitrogen atom in the 1 H– 15 N gs -HMBC spectrum (in 7a ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Bis(1,2,3-Triazole) Functionalized Quinoline-2,4-Diones

et al. 2018

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Derivatives of 3-(1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione unsubstituted on quinolone nitrogen atom, which are available by the previously described four step synthesis starting from aniline, were exploited as intermediates in obtaining the title compounds. The procedure involves the introduction of propargyl group onto the quinolone nitrogen atom of mentioned intermediates by the reaction of them with propargyl bromide in N,N-dimethylformamide (DMF) in presence of a potassium carbonate and the subsequent formation of a second triazole ring by copper catalyzed cyclisation reaction with azido compounds. The products were characterized by 1H, 13C and 15N NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (1H–1H gs-COSY, 1H–13C gs-HSQC, 1H–13C gs-HMBC) with 1H–15N gs-HMBC as a practical tool to determine 15N NMR chemical shifts at the natural abundance level of 15N isotope.

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“…For the first published synthesis of the title compound, see: Rapoport & Holden (1959). For recent synthetic utilization of 3-alkyl-4-hydroxyquinolin-2-ones, see, for example: Kimmel et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

3-Ethyl-4-hydroxy-8-methoxyquinolin-2(1H)-one

et al. 2012

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Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.005 Å; R factor = 0.077; wR factor = 0.272; data-to-parameter ratio = 15.9.In the title compound, C 12 H 13 NO 3 , the quinoline ring system is approximately planar with a maximum deviation from the least-squares plane of 0.058 (2) Å . In the crystal, N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds link the molecules into chains running along the b-axis direction. The chains also featureinteractions between pyridine and benzene rings of inversionrelated molecules [centroid-centroid distance = 3.609 (2) Å ].

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Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

Cited by 14 publications

References 69 publications

Development of Novel Galactosylated PLGA Nanoparticles for Hepatocyte Targeting Using Molecular Modelling

Development of Novel Galactosylated PLGA Nanoparticles for Hepatocyte Targeting Using Molecular Modelling

Synthesis of Bis(1,2,3-Triazole) Functionalized Quinoline-2,4-Diones

3-Ethyl-4-hydroxy-8-methoxyquinolin-2(1H)-one

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