Microwave-assisted preparation, structural characterization, lipophilicity, and anti-cancer assay of some hydroxycoumarin derivatives

ABSTRACT: A new series of hydroxycoumarin derivatives has been synthesized using conventional synthesis. The syntheses were accelerated by microwave assistance. Yields in both cases were comparable (59–69 %). The structures were established by (1)H and (13)C NMR spectroscopy and high-resolution mass...

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Detalles Bibliográficos
Autores principales: Ostrowska, Kinga, Hejchman, Elżbieta, Maciejewska, Dorota, Włodarczyk, Agata, Wojnicki, Kamil, Matosiuk, Dariusz, Czajkowska, Agnieszka, Młynarczuk-Biały, Izabela, Dobrzycki, Łukasz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2014
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4494852/
https://www.ncbi.nlm.nih.gov/pubmed/26166896
http://dx.doi.org/10.1007/s00706-014-1320-8
Descripción
Sumario:ABSTRACT: A new series of hydroxycoumarin derivatives has been synthesized using conventional synthesis. The syntheses were accelerated by microwave assistance. Yields in both cases were comparable (59–69 %). The structures were established by (1)H and (13)C NMR spectroscopy and high-resolution mass spectrometry. Five compounds (5-hydroxy-4,7-dimethylcoumarin, 6-acetyl-5-hydroxy-4,7-dimethylcoumarin, 4-(cyanomethoxy)chromen-2-one, 5-(cyanomethoxy)-4,7-dimethylchromen-2-one, and 6-acetyl-5-(cyanomethoxy)-4,7-dimethylchromen-2-one) were assayed for anti-cancer activity. For all presented coumarin derivatives, lipophilicity was measured using reversed-phase TLC in different eluent systems with standardization. In addition, the crystal structure of 6-acetyl-5-hydroxy-4,7-dimethylcoumarin has been solved by X-ray structure analysis of single crystals. GRAPHICAL ABSTRACT: [Image: see text]

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