Next Article in Journal
The Stimulatory Effects of Nanochitin Whisker on Carbon and Nitrogen Metabolism and on the Enhancement of Grain Yield and Crude Protein of Winter Wheat
Next Article in Special Issue
Synthesis and Cytotoxic Evaluation of 3-Methylidenechroman-4-ones
Previous Article in Journal
Correction: Ding, S., et al. NNB-Type Tridentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C–H Borylation. Molecules 2019, 24, 1434
Previous Article in Special Issue
Synthesis of Novel Pyrazole Derivatives and Their Tumor Cell Growth Inhibitory Activity
Open AccessFeature PaperArticle

4,5-Diaryl 3(2H)Furanones: Anti-Inflammatory Activity and Influence on Cancer Growth

1
Skolkovo Institute of Science and Technology, Skolkovo Innovation Center, 3 Nobel Street, 143026 Moscow, Russia
2
Moscow Institute of Physics and Technology, 9 Institutsky lane, 141700 Dolgoprudny, Russia
3
Saint-Petersburg State University, Institute of Chemistry, Universitetskiy Prospekt, 26, 198504 Petergof, Russia
4
Department of Pharmacology, School of Pharmacy, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece
5
Department of Medical Laboratory Studies, School of Health and Medical Care, Alexander Technological Educational Institute of Thessaloniki, 57400 Thessaloniki, Greece
6
Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(9), 1751; https://doi.org/10.3390/molecules24091751
Received: 1 April 2019 / Revised: 24 April 2019 / Accepted: 30 April 2019 / Published: 6 May 2019
(This article belongs to the Special Issue Design and Synthesis of Organic Molecules as Antineoplastic Agents)
Apart from their anti-inflammatory action, COX inhibitors have gathered the interest of many scientists due to their potential use for the treatment and prevention of cancer. It has been shown that cyclooxygenase inhibitors restrict cancer cell growth and are able to interact with known antitumor drugs, enhancing their in vitro and in vivo cytotoxicity. The permutation of hydrophilic and hydrophobic aryl groups in COX inhibitors leads to cardinal changes in the biological activity of the compounds. In the present study, thirteen heterocyclic coxib-like 4,5-diarylfuran-3(2H)-ones and their annelated derivatives—phenanthro[9,10-b]furan-3-ones—were synthesized and studied for anti-inflammatory and COX-1/2 inhibitory action and for their cytotoxic activity on the breast cancer (MCF-7) and squamous cell carcinoma (HSC-3) cell lines. The F-derivative of the –SOMe substituted furan-3(2H)-ones exhibited the best activity (COX-1 IC50 = 2.8 μM, anti-inflammatory activity (by carrageenan paw edema model) of 54% (dose 0.01 mmol/kg), and MCF-7 and HSC-3 cytotoxicity with IC50 values of 10 μM and 7.5 μM, respectively). A cytotoxic effect related to the COX-1 inhibitory action was observed and a synergistic effect with the anti-neoplastic drugs gefitinib and 5-fluorouracil was found. A phenanthrene derivative exhibited the best synergistic effect with gefitinib. View Full-Text
Keywords: 3(2H)furanones; phenanthro[9,10-b]furanones; cyclooxygenase; cytotoxicity; anticancer; MCF-7; HSC-3; gefitinib; 5-fluorouracil 3(2H)furanones; phenanthro[9,10-b]furanones; cyclooxygenase; cytotoxicity; anticancer; MCF-7; HSC-3; gefitinib; 5-fluorouracil
Show Figures

Figure 1

MDPI and ACS Style

Semenok, D.; Medvedev, J.; Giassafaki, L.-P.; Lavdas, I.; Vizirianakis, I.S.; Eleftheriou, P.; Gavalas, A.; Petrou, A.; Geronikaki, A. 4,5-Diaryl 3(2H)Furanones: Anti-Inflammatory Activity and Influence on Cancer Growth. Molecules 2019, 24, 1751.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop