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Download This Article PDF Format RSC Advances View Article Online PAPER View Journal | View Issue 2,3-Disubstituted-1,4-naphthoquinones containing an arylamine with trifluoromethyl group: synthesis, Cite this: RSC Adv.,2017,7, 25753 biological evaluation, and computational study† a a b c Hatice Yıldırım, * Nilufer¨ Bayrak, Amac Fatih Tuyun, * Emel Mataracı Kara, Berna Ozbek¨ Çelikc and Girish Kumar Gupta d Antibacterial and antifungal organic compounds are becoming increasingly important for biomedical applications. This study deals with the synthesis, characterization of structures, in silico PASS prediction, and the discovery of antibacterial and antifungal properties based on new sulfanyl-1,4-naphthoquinone derivatives containing an arylamine with a trifluoromethyl group at different positions, which can be further applied in drug discovery and development. The in vitro antimicrobial potential of the newly synthesized compounds was evaluated in a panel of seven bacterial strains (three Gram-positive and four Gram-negative bacteria) and one yeast, with an additional study on antibiofilm activities. The compounds Creative Commons Attribution-NonCommercial 3.0 Unported Licence. (5b and 5e) were identified as having strong antibacterial efficiency against the human-originated pathogen S. epidermidis, with minimal inhibitory concentration values (4.88 and 2.44 mgmLÀ1, respectively). The toxicity of both compounds (5b and 5e) was studied in detail to compare these compounds with Cefuroxime (a clinically proven drug). The antibacterial activity of the compound 5f was equal to that of Cefuroxime. Moreover, three compounds (5b, 5e, and 5f) exhibited excellent Received 20th January 2017 antibacterial activity, and 5b and 5e were two and four times more active than the reference Accepted 18th April 2017 antimicrobial compound (Cefuroxime), respectively. For this reason, these three compounds (5b, 5e, and DOI: 10.1039/c7ra00868f 5f) are being considered as promising antibacterial agents. In addition, docking studies were used to rsc.li/rsc-advances better rationalize the action and prediction of the binding modes of these compounds. This article is licensed under a malaria, other pathogens, and infections that have been 1. Introduction 1a,2 Open Access Article. Published on 12 May 2017. Downloaded 9/27/2021 9:13:25 PM. causing the majority of deaths since 2010. Although there has been a decline in the incidence of infectious Infectious diseases are among the most serious threats of the diseases, there is no place in the world where infectious “top global health risk factors”, just like the high risk factors of diseases are an insignicant cause of illness and death.1,2 The chemical spills and nuclear accidents.1b,c,2,3 WHO has, therefore, number of deaths caused by pathogens and parasites have provided effective global strategies for the control of major shown a minor decline of only 1% per year. Over 10 million infectious diseases that are being dubbed as the “infectious people have died from infections since 1990.1a,2 The World diseases control programs”, which are necessary in order to Health Organization (WHO) estimates 13 million deaths from help build these health systems.4 infectious diseases in 2050.2 People in low- and middle-income The fact that the resistance of bacterial and fungal patho- countries suffer from diseases such as HIV/AIDS, tuberculosis, gens leads to an ever-increasing global public health threat reects the widespread and growing demand for new antibac- terial and antifungal compounds, which are among the most aChemistry Department, Engineering Faculty, Istanbul University, Avcilar, 34320, prevalently used drugs.5 Unfortunately, very few new classes of Istanbul, Turkey. E-mail: [email protected]; Fax: +90 212 473 7180; Tel: antibacterial drugs have been registered for clinical practice in +90 212 473 7070 6 b the past 50 years. Not surprisingly, this has recently caused Engineering Sciences Department, Engineering Faculty, Istanbul University, Avcilar, ffi 34320, Istanbul, Turkey. E-mail: [email protected]; [email protected]; Fax: a rapidly growing interest in the synthesis of new and e cient +90 212 473 7180; Tel: +90 212 473 7070 antibacterial and antifungal compounds that may be drug cPharmaceutical Microbiology Department, Pharmacy Faculty, Istanbul University, candidates for reducing infections caused by pathogens.7 Beyazit, 34116, Istanbul, Turkey The antimicrobial activities of an increasing number of dDepartment of Pharmaceutical Chemistry, Maharishi Markandeshwar College of quinone compounds are being investigated for the discovery of Pharmacy, Maharishi Markandeshwar University, Mullana, Ambala 133207, new antibacterial and antifungal compounds.7,8 A series of Haryana, India † Electronic supplementary information (ESI) available. See DOI: sulfanyl-1,4-naphthoquinone derivatives was synthesized and 10.1039/c7ra00868f potent antifungal activity was exhibited in vitro by one This journal is © The Royal Society of Chemistry 2017 RSC Adv.,2017,7, 25753–25764 | 25753 View Article Online RSC Advances Paper compound, compared to the clinically proven antifungal drug uconazole, against S. schenckii, and the clinically proven drug amphotericin-B against T. mentagraphytes.9 1,4-Naph- thoquinones containing an amino group have been used as antibacterials, antimalarials, antituberculars, larvicides and molluscicides, herbicides, and fungicides in many medical and biological applications.10–14 A series of phenylamino-1,4- naphthoquinones was synthesized to investigate their anti- tumor effects against cancer cell lines and healthy broblasts, and it was reported that the presence of a chlorine atom in the acceptor quinone nucleus and/or the presence of a methyl group at the nitrogen atom of the donor phenylamino group induced changes in cytotoxic activity.15 Since the triuoromethyl group (–CF3) is one of the most important substituents in organic chemistry because of its interesting stereoelectronic prole,16 our attention was turned to the naphthoquinone compounds containing the –CF3 on the arylamines at the o-, m-, and p-positions, in light of previous 17 À ff ff studies. The CF3 has an e ect based on the di erent electron density distributions on the reactivity of the molecule. The efficiency of –CF3 on the physiological activity is a very signi- cant topic in pharmaceutical studies. The physiological prole – Creative Commons Attribution-NonCommercial 3.0 Unported Licence. is dependent on the position of CF3 within the bioactive molecules.16 Fig. 1 Structures of some nitro free and nitro substituted aminonaphthoquinones.17 A series of naphthoquinone derivatives has been synthesized and tested for their biological activity against human African trypanosomiasis, normally known as sleeping sickness, a dangerous and oen ignored parasitic disease.17 The activities of some compounds have been compared to evaluate the importance of the position of the –CF3 group on the phenyl amine ring and its substitution that caused by the inhibition of This article is licensed under a T. brucei cell proliferation. Compounds shown in Fig. 1 with –CF3 (electron withdrawing group) at different positions on the phenyl amine ring showed T. brucei inhibitory activity with Open Access Article. Published on 12 May 2017. Downloaded 9/27/2021 9:13:25 PM. average cytotoxicity. It was found that the presence of a chlorine atom instead of a second arylamine led to an increase in the activity. Additionally, changing the –CF3 from the para position to the ortho position led to an increase in the activity. It was reported that the reason for this enhancement in T. brucei inhibitory activity might have been the strong electron with- Fig. 2 Structures of some important sulfanyl aminonaphthoquinones with biological activity in literature. drawing groups (–CF3, –NO2, and Cl) within the structure; – ff replacing the CF3 with the methyl group at di erent positions led to activity loss. In this study, it can be clearly seen that the substitution patterns (2nd and 4th positions) on aniline and synthesized other series of sulfanyl aminonaphthoquinone monoamino- or diamino-substituted compounds affect the T. and aminonaphthoquinone derivatives, and the synthesized brucei inhibitory activity.17 compounds were tested for antibacterial and antifungal activi- Sulfanyl aminonaphthoquinone and aminonaphthoquinone ties. Particularly, sulfanyl aminonaphthoquinone derivatives derivatives have important applications in medicinal chemistry containing the arylsulfanyl group did not exhibit any signicant as biologically active substances. Among them, some most activity (VII). In this study, the antifungal activity was observed striking examples are shown in Fig. 2. Tandon et al. reported the to decrease when the 2,3-disubstituted moiety was altered by synthesis of some sulfanyl aminonaphthoquinone compounds the phenyl group.8b (I–IV) and their biological evaluation. Some of these compounds There are several factors that affect the biological evaluation showed signicant antibacterial activity.7c,d Very recently, of the quinone structures, which are listed as follows: (a) another research study on the synthesis of the sulfanyl aryla- a naphthoquinoidal moiety; (b) an aromatic ring such as mino quinone compounds was reported by Ryu et al. Some of aniline; (c) the presence and position of substituents on the the tested compounds (V and VI) completely inhibited fungal phenyl amine ring, and insertion of additional electronegative growth when compared to the Candida species.8a Tandon et al. atoms (Cl, S, N etc.).15,17,18
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