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Open AccessArticle

Synthesis and Antitumor Activity Evaluation of Compounds Based on Toluquinol

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Department of Organic Chemistry, Faculty of Sciences, University of Málaga, Campus de Teatinos s/n, 29071 Málaga, Spain
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Department of Molecular Biology and Biochemistry, Faculty of Sciences, University of Málaga, Campus de Teatinos s/n, 29071 Málaga, Spain
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IBIMA (Biomedical Research Institute of Málaga), 29071 Málaga, Spain
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CIBER of Rare Diseases; Group U741 (CB06/07/0046), 29071 Málaga, Spain
*
Authors to whom correspondence should be addressed.
Iván Cheng-Sánchez and José A. Torres-Vargas contributed equally to the execution of this work.
Mar. Drugs 2019, 17(9), 492; https://doi.org/10.3390/md17090492
Received: 28 July 2019 / Revised: 14 August 2019 / Accepted: 18 August 2019 / Published: 23 August 2019
(This article belongs to the Special Issue Synthetic and Biosynthetic Approaches to Marine Natural Products)
Encouraged by the promising antitumoral, antiangiogenic, and antilymphangiogenic properties of toluquinol, a set of analogues of this natural product of marine origin was synthesized to explore and evaluate the effects of structural modifications on their cytotoxic activity. We decided to investigate the effects of the substitution of the methyl group by other groups, the introduction of a second substituent, the relative position of the substituents, and the oxidation state. A set of analogues of 2-substituted, 2,3-disubstituted, and 2,6-disubstituted derived from hydroquinone were synthesized. The results revealed that the cytotoxic activity of this family of compounds could rely on the hydroquinone/benzoquinone part of the molecule, whereas the substituents might modulate the interaction of the molecule with their targets, changing either its activity or its selectivity. The methyl group is relevant for the cytotoxicity of toluquinol, since its replacement by other groups resulted in a significant loss of activity, and in general the introduction of a second substituent, preferentially in the para position with respect to the methyl group, was well tolerated. These findings provide guidance for the design of new toluquinol analogues with potentially better pharmacological properties. View Full-Text
Keywords: toluquinol; thymoquinone; marine hydroquinone; antitumor; natural compound analogues toluquinol; thymoquinone; marine hydroquinone; antitumor; natural compound analogues
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MDPI and ACS Style

Cheng-Sánchez, I.; Torres-Vargas, J.A.; Martínez-Poveda, B.; Guerrero-Vásquez, G.A.; Medina, M.Á.; Sarabia, F.; Quesada, A.R. Synthesis and Antitumor Activity Evaluation of Compounds Based on Toluquinol. Mar. Drugs 2019, 17, 492.

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