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

作者：Ostrowska Kinga^*; Hejchman Elzbieta; Maciejewska Dorota; Wlodarczyk Agata; Wojnicki Kamil; Matosiuk Dariusz; Czajkowska Agnieszka; Mlynarczuk Bialy Izabela; Dobrzycki Lukasz

来源：Monatshefte fur Chemie, 2015, 146(1): 89-98.

DOI：10.1007/s00706-014-1320-8

• Hydroxycoumarin
• Microwave-assisted synthesis
• Lipophilicity Anti-cancer activity
• X-ray structure

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 H-1 and C-13 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.

• 出版日期2015-1