Synthesis, structural characterization and biological activity of novel Knoevenagel condensates on DLD-1 human colon carcinoma

[Display omitted] Biologically active Knoevenagel condensates (1–14) of diarylheptanoids: 1,7-bis(3-methoxy-4-hydroxyphenyl)hepta-1,7-diene-3,5-dione and 1,7-bis(3-ethoxy-4-hydroxyphenyl)hepta-1,7-diene-3,5-dione, were synthesized and structurally characterized. Compounds 1–14 exhibited cytotoxicity...

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Published in:Bioorganic & medicinal chemistry letters 2017-06, Vol.27 (11), p.2345-2349
Main Authors: Rišiaňová, Lucia, Fischer-Fodor, Eva, Valentová, Jindra, Tatomir, Corina, Corina Decea, Nicoleta, Virag, Piroska, Pechová, Iveta, Devínsky, Ferdinand, Miklášová, Natalia
Format: Article
Language:English
Subjects:
Antineoplastic Agents - pharmacology
Antioxidant activity
Cell Line, Tumor
Cell Proliferation - drug effects
Colonic Neoplasms - pathology
Curcuminoids
Cytotoxicity
Diarylheptanoids - chemistry
Diarylheptanoids - pharmacology
Humans
Knoevenagel condensates
Multidrug resistance
SOD-mimetic activity
Superoxide Dismutase - metabolism
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Summary:[Display omitted] Biologically active Knoevenagel condensates (1–14) of diarylheptanoids: 1,7-bis(3-methoxy-4-hydroxyphenyl)hepta-1,7-diene-3,5-dione and 1,7-bis(3-ethoxy-4-hydroxyphenyl)hepta-1,7-diene-3,5-dione, were synthesized and structurally characterized. Compounds 1–14 exhibited cytotoxicity against colon carcinoma cells, and their antiproliferative effect was associated with a significant decrease of multidrug resistance proteins. One of the underlying mechanisms of these effects is the reduction of intracellular and extracellular SOD enzymes by compounds 1, 12 and 14, which render the tumor cells more vulnerable to oxidative stress.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2017.04.031