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Chalcones: Synthetic Chemistry Follows Where Nature Leads

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Chalcones: Synthetic Chemistry Follows Where Nature Leads biomolecules Review Chalcones: Synthetic Chemistry Follows Where Nature Leads Hiba A. Jasim 1,2 , Lutfun Nahar 3,* , Mohammad A. Jasim 4 , Sharon A. Moore 5 , Kenneth J. Ritchie 1,* and Satyajit D. Sarker 1 1 Centre for Natural Products Discovery (CNPD), School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UK; [email protected] (H.A.J.); [email protected] (S.D.S.) 2 Department of Biology, College of Education for Pure Sciences, University of Anbar, Al-Anbar 10081, Iraq 3 Laboratory of Growth Regulators, Institute of Experimental Botany ASCR & Palacký University, Šlechtitel ˚u27, 78371 Olomouc, Czech Republic 4 Department of Biology, College of Education for Women, University of Anbar, Al-Anbar 10081, Iraq; [email protected] 5 Faculty of Science and Engineering, University of Wolverhampton, Wolverhampton WV1 1LY, UK; [email protected] * Correspondence: [email protected] (L.N.); [email protected] (K.J.R.); Tel.: +44-(0)-1512312219 (K.J.R.) Abstract: Chalcones belong to the flavonoid class of phenolic compounds. They form one of the largest groups of bioactive natural products. The potential anticancer, anti-inflammatory, antimi- crobial, antioxidant, and antiparasitic properties of naturally occurring chalcones, and their unique chemical structural features inspired the synthesis of numerous chalcone derivatives. In fact, struc- tural features of chalcones are easy to construct from simple aromatic compounds, and it is convenient to perform structural modifications to generate functionalized chalcone derivatives. Many of these synthetic analogs were shown to possess similar bioactivities as their natural counterparts, but Citation: Jasim, H.A.; Nahar, L.; often with an enhanced potency and reduced toxicity. This review article aims to demonstrate how Jasim, M.A.; Moore, S.A.; Ritchie, K.J.; bioinspired synthesis of chalcone derivatives can potentially introduce a new chemical space for Sarker, S.D. Chalcones: Synthetic exploitation for new drug discovery, justifying the title of this article. However, the focus remains on Chemistry Follows Where Nature Leads. Biomolecules 2021, 11, 1203. critical appraisal of synthesized chalcones and their derivatives for their bioactivities, linking to their https://doi.org/10.3390/ interactions at the biomolecular level where appropriate, and revealing their possible mechanisms biom11081203 of action. Academic Editor: Vladimir Keywords: chalcones; biomolecular interactions; synthesis; natural products; bioactivities; mecha- N. Uversky nisms; anticancer; antimicrobial; phenolics Received: 31 July 2021 Accepted: 11 August 2021 Published: 13 August 2021 1. Introduction Chalcones are flavonoid-type phenolic phytochemicals, often referred to as ‘open- Publisher’s Note: MDPI stays neutral chain flavonoids’, and biosynthesized via the shikimate pathway [1]. Chalcones are con- with regard to jurisdictional claims in sidered as the biosynthetic precursors of flavonoids. Chemically, chalcones are generally published maps and institutional affil- α,β-unsaturated ketones consisting of two aromatic rings (rings A and B) linked through a iations. three-carbon alkenone unit (Figure1), but these may also include some saturated ketones, commonly known as dihydrochalcones, where instead of a three-carbon alkenone unit, a three-carbon alkanone unit is present. Among the naturally occurring chalcones, the presence of one or more phenolic hydroxyl functionalities is ubiquitous, and prenyl and Copyright: © 2021 by the authors. geranyl substitutions on the aromatic rings are also widely observed. There are several Licensee MDPI, Basel, Switzerland. thousand naturally occurring chalcones reported in the literature [2], and many of those This article is an open access article chalcones were shown to interact with various biomolecules and possess cytoprotective and distributed under the terms and modulatory properties, making them potentially suitable candidates for therapeutic inter- conditions of the Creative Commons ventions in many human ailments. Several patents are also available for chalcones and their Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ derivatives for their activities as anticancer, anti-inflammatory, antimitotic, antioxidant, 4.0/). and cytotoxic properties [3]. Biomolecules 2021, 11, 1203. https://doi.org/10.3390/biom11081203 https://www.mdpi.com/journal/biomolecules Biomolecules 2021, 11, x FOR PEER REVIEW 2 of 38 Biomolecules 2021, 11, x FOR PEER REVIEW 2 of 38 Biomolecules 2021, 11, x FOR PEER REVIEW 2 of 38 BiomoleculesBiomolecules Biomolecules 20212021 20212021,, 1111,, ,11,11 1203x, , FOR xx FORFOR PEER PEERPEER REVIEW REVIEWREVIEW 2 of22 of 37of38 38 38 Biomolecules 2021, 11, x FOR PEER REVIEW 2 of 38 B β B β B BB ββ α A β A α B A α B A α B AAA β α AAA α α BB α αα β B A A α β B α or β ββ or or oror β Figure 1. General structure of chalcones. Figure 1. General structure or of chalcones. FigureFigureFigure 1. 1.1.General GeneralGeneral structure structurestructure of of ofchalcones. chalcones.chalcones. FigureBecause 1. General of structure structural of chalcones. simplicity and therapeutic potential, several bioinspired syn- Because of structural simplicity and therapeutic potential, several bioinspired syn- thesesBecauseBecauseBecause of chalcone of of of structural structuralstructural derivatives simplicity simplicitysimplicity and evaluation and andand therapeutic therapeutictherapeutic of their potential, potential,bioactivitiespotential, several severalseveral were bioinspired bioinspiredbioinspiredreported insyn- syn-syn-the theses of chalcone derivatives and evaluation of their bioactivities were reported in the thesesliteraturethesesthesesBecause of of of chalcone [2]. chalconechalcone of The structural first derivatives derivativesderivatives few simplicity attempts and andand evaluation forevaluationandevaluation th therapeutice synthesis of of of their theirtheir ofpotential, bioactivities chalcobioactivitiesbioactivitiesnes several began were werewere bioinspired in reported reportedreportedthe 1800 in ′ syn-sin in theand thethe literature [2]. 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