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Molecules 2014, 19(7), 9655-9674; doi:10.3390/molecules19079655

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

1
Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece
2
Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece
3
Symeonidion Research Center, "Theagenion" Cancer Hospital, Thessaloniki, 54007, Greece
*
Authors to whom correspondence should be addressed.
Received: 5 May 2014 / Revised: 13 June 2014 / Accepted: 17 June 2014 / Published: 7 July 2014
(This article belongs to the Special Issue Natural Antioxidants and Ageing)
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Abstract

Cinnamic acids have been identified as interesting compounds with antioxidant, anti-inflammatory and cytotoxic properties. In the present study, simple cinnamic acids were synthesized by Knoevenagel condensation reactions and evaluated for the above biological activities. Compound 4ii proved to be the most potent LOX inhibitor. Phenyl- substituted acids showed better inhibitory activity against soybean LOX, and it must be noted that compounds 4i and 3i with higher lipophilicity values resulted less active than compounds 2i and 1i. The compounds have shown very good activity in different antioxidant assays. The antitumor properties of these derivatives have been assessed by their 1/IC50 inhibitory values in the proliferation of HT-29, A-549, OAW-42, MDA-MB-231, HeLa and MRC-5 normal cell lines. The compounds presented low antitumor activity considering the IC50 values attained for the cell lines, with the exception of compound 4ii. Molecular docking studies were carried out on cinnamic acid derivative 4ii and were found to be in accordance with our experimental biological results. View Full-Text
Keywords: antioxidant activity; inflammation; cancer; lipoxygenase; cinnamic acids; molecular docking antioxidant activity; inflammation; cancer; lipoxygenase; cinnamic acids; molecular docking
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Pontiki, E.; Hadjipavlou-Litina, D.; Litinas, K.; Geromichalos, G. Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies. Molecules 2014, 19, 9655-9674.

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