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Chalcone Derivatives and Their Antibacterial Activities Current Bioorganic Chemistry 91 (2019) 103133 Contents lists available at ScienceDirect Bioorganic Chemistry journal homepage: www.elsevier.com/locate/bioorg Chalcone derivatives and their antibacterial activities: Current development T ⁎ Man Xu, Piye Wu, Fan Shen, Jiayou Ji, K.P. Rakesh Engineering Research Center of Environmental Materials and Membrane Technology of Hubei Province, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, PR China ARTICLE INFO ABSTRACT Keywords: The increase in antibiotic resistance due to various factors has encouraged the look for novel compounds which Chalcones are active against multidrug-resistant pathogens. In this framework, chalcone-based compounds showed a di- Antibacterial activity versity of pharmacological properties, and its derivatives possess a high degree of structural diversity, and it is SAR studies helpful for the discovery of new therapeutic agents. The growing resistance to antibiotics worldwide has en- dangered their efficacy. This has led to a surging interest in the discovery of new antibacterial agents. Thus,there is an urgent need for new antibacterial drug candidates with increased strength, new targets, low cost, superior pharmacokinetic properties, and minimum side effects. The present review concluded and focuses on the recent developments in the area of medicinal chemistry to explore the diverse chemical structures of potent anti- bacterial agents and also describes its structure-activity relationships studies. The various synthetic structures leading to this class of neutral protective compound is common and additional structural optimization is pro- mising for potential drug discovery and development. 1. Introduction therapeutic molecule is very significant to be introduced as antibiotic for the treatment of multi-drug resistance MRSA [7,8]. Even though the The damage of bacterial and fungal infections has increased hugely MRSA presence in the human flora of skin and especially nasal mucosa, in recent years [1]. Infectious diseases caused by bacterial pathogens it is an opportunistic pathogen frequently found in nosocomial infec- have become a main public health problem due to the extensive oc- tions that may lead to severe infections, including septicemias [9]. currence of drug resistance. Resistance to antimicrobial agents has in- S. aureus is one of the main human pathogen cause’s soft external creased health concerns and resulted in mortality and morbidity from infections to harsh life-threatening persistent infections to the human treatment failures [2,3]. Several bacterial strains causing infectious world ensuing in important morbidity and mortality [10–16]. The S. diseases which seemed to be in control are once again causing death aureus growing on living or inert surfaces as biofilms, which is com- every year due to the absence of suitable antibiotic drug [4]. Re- munity having closely packed S. aureus cells bounded with self-secreted grettably, the development of new antibiotics has failed to keep pace matrix [17]. The biofilm play an important role in antibiotic drug re- with the development of drug-resistance over the past few decades [5]. sistance which leads to public hazard worldwide [18]. In the past few Thus, there is a critical global healthcare crisis, which requires the decades, the number of efforts has been made in the medicinal chem- urgent development of more effective antibiotics. In particular, atten- istry through synthetic tailoring in a combinatorial fashion, to generate tion has focused on the Gram positive organism Staphylococcus aureus a large set of analogues as core scaffolds. While the tremendous ap- because many strains of this organism are now resistant against clini- proaches have been successful, no new major class of antibiotics were cally useful antibiotics like methicillin and vancomycin [6]. invented between 1962 and 2000 [19]. Therefore, to come up with new The occurrence of multi-drug resistant bacteria becomes a severe effective therapeutic agents, there is a need for aggressive efforts andit medical setback in hospital and community settings [2]. Among them, is imperative to discover novel synthetic entities for the microbial MRSA (methicillin-resistant Staphylococcus aureus), penicillin resistant target is a big challenge to the medicinal chemistry [20,21]. The overall Streptococcus pneumoniae (PRSP), and vancomycin resistant Enterococci clinical experiences reveal that the single-targeted drugs will not be (VRE) are leading concerns. In addition, this can be caused due to effective agents to the biological system even if they have goodin- routine dealing of non-bacterial infections antibiotics and insufficient hibitory activity against specific target [22,23]. completion with the system for drug intake. In this position, the new Chalcones is an open-chain flavonoid with α,β-unsaturated carbonyl ⁎ Corresponding author. E-mail address: [email protected] (K.P. Rakesh). https://doi.org/10.1016/j.bioorg.2019.103133 Received 29 April 2019; Received in revised form 27 June 2019; Accepted 18 July 2019 Available online 19 July 2019 0045-2068/ © 2019 Elsevier Inc. All rights reserved. M. Xu, et al. Bioorganic Chemistry 91 (2019) 103133 group and is one of the important compound groups of flavonoid de- the generation of compound 5 (Fig. 1). Recently, triazolyl bearing rived from nature and synthetic compounds belonging to the flavonoid chalcone 6 (Fig. 1) was synthesized and evaluated [53] against a panel family which remain a fascination among researchers in the 21st cen- of bacterial (MRSA, S. aureus, B. subtilis, M. luteus, E. coli, B. typhi, P. tury due to their simple chemistry, ease of synthesis, large number of aeruginosa, and B. proteus) strains. The most active compound 6 dis- replaceable hydrogens to yield a variety of derivatives. Due to their played maximum activity against MRSA (MIC: 4 µg/mL), M. luteus abundance in plants and ease of synthesis, this class of compounds has (MIC: 4 µg/mL) and C. mycoderma (MIC: 8 µg/mL) comparable or better generated great interest for possible therapeutic uses [24]. Thousands than the control drugs (Chloromycin and Norfloxacin). of chalcone derivatives are synthesized in chemical laboratories, up to date. Chalcones containing several functional groups showed a wide 2.2. Antibacterial activity of chlorinated chalcones spectrum of biological activities such as antimicrobial [25–28], anti- malarial [29,30], anticancer [31,32], anti-inflammatory [33,34], anti- The SAR of 2-((5E)-5-(4-((E)-3-(2,4-dichlorophenyl)-3-oxoprop-1- protozoal [35], anti-HIV [36], antioxidant [37] and antiulcer [38] ac- enyl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid hybrid 7 tivities. Chalcones and their derivatives have also been found to display (Fig. 2) was found to be most potent antibacterial activity against S. antioxidant [39], antimicrobial [40], anticancer [41], anti-malarial aureus with MIC value of 2 µg/mL, which was better than the standard [42], anti-inflammatory [43], antiulcer [44], antileishmanial [45] and drug (norfloxacin; but less active than oxacillin) indicated that thein- anti-HIV [46] properties. troduction of strong electron-withdrawing chloro groups at 2 and 4- We believe, this review article will be useful for inspiring the design, position of phenyl ring increased the anti bacterial activity. While the structural-activity relationship and developments of less toxic, low cost incorporation of electron-donating (p-CH3, 2,4-(CH3)2, m-OCH3, p- and powerful chalcone-based drugs against the various types of bac- OCH3, m-OCH2OCH3, p-OCH2OCH3) groups on the phenyl ring reduced terial infectious diseases. the antibacterial activity. Comparing the derivatives with different chloro-substitution positions on the phenyl ring, their activity order 2. Antibacterial properties of chalcone derivatives was 2,4-Cl2 > p-Cl > m-Cl > o-Cl [54]. This suggests that the in- troduction of two atoms of the halogens to the hybrid compound may 2.1. Antibacterial activity of fluorinated chalcones have played an important part in increasing anti-bacterial properties, for which more compounds using 7 as the lead compound need to be Fluorine has become an important tool in drug discovery, since designed and synthesized for further investigation. incorporation of fluorine atom or fluorinated group into drugs ordrug The electron-withdrawing substituents (eNO2) on benzene ring lead allows simultaneous modulations of electronic, liphophilic, steric displayed superior activity than electron-donating (eOH and eOMe) parameters all of which can critically influence both the phar- groups [55]. The substituent at R position of quinazolinone-chalcone amcokinatics and pharmacodynamic properties of drugs [47,48]. Thus, hybrids played an important role in antibacterial activity of hybrid 8 integration of fluorinated chalcone-1,2,3-triazole hybrids might exhibit (Fig. 2; IC50 = 0.125 mg/mL against S. aureus and S. pyogenes) showed synergetic effect in enhancing the bio-activity of these derivatives. excellent antibacterial activities and which is more potent than stan- Based on the above consideration, a novel series of fluorinated chal- dard antibacterial drug Ciprofloxacin (IC50 = 0.5–1.0 mg/mL). The cone-1,2,3-triazole hybrids were designed, synthesized and tested for in SAR revealed that the position of bromine atom on the benzene ring is vitro antibacterial activities against S. epidermidis, B. subtilis, E. coli and highly favoured for antibacterial activity. On the other hand,
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