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Synthesis and pharmacological activity of O-aminoalkyl derivatives of 7-hydroxycoumarin.

European journal of medicinal chemistry (2011-03-29)
Joanna Trykowska Konc, Elżbieta Hejchman, Hanna Kruszewska, Irena Wolska, Dorota Maciejewska
ABSTRACT

A series of novel O-aminoalkyl substituted 7-hydroxycoumarins were synthesized and evaluated for antibacterial and anticancer toxicity. Two different synthetic procedures, conventional and microwave assisted were used, and the structures of the compounds were confirmed by IR, 1H, 13C NMR and MAS spectroscopic data. The molecular and crystal structures of 8-acetyl-7-[2-(1-morpholino)ethoxy]4-methylchromen-2-one in solid state were analyzed by single crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P2(1)/c. The main driving forces for the supramolecular structure are the C-H⋯O hydrogen bonds and the π⋯π intermolecular interactions. The most active compounds are those, where the O-aminoalkyl substituent has N,N-diethylamino part, and acetyl group is at C6 or at C8 atoms.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
4-Methylumbelliferone, ≥98%
Sigma-Aldrich
Umbelliferone, 99%
Sigma-Aldrich
Umbelliferone, suitable for fluorescence indicator, ≥98.0% (HPLC)

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