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Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring And/Or Brominated Substituents

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Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring And/Or Brominated Substituents Title of the Article Journal Name, 2014, Vol. 0, No. 0 1 Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring and/or Brominated Substituents Renzo Rossi*a, Marco Lessi,a Chiara Manzini,a Giulia Marianetti,b Fabio Bellina*a aDipartimento di Chimica e Chimica Industriale, Università di Pisa, Pisa, Italy bScuola Normale Superiore, Piazza dei Cavalieri 7, Pisa, Italy Abstract: This review with 263 references deals with the synthesis of unnatural and natural 2(5H)-furanone derivatives featuring bromine atoms on the heterocyclic ring and/or brominated substituents, which have been described in the literature since 1951 up to February 2016. The review has been organized on the basis of seven classes of brominated furanone derivatives that were synthesized. Where possible, experimental details of the syntheses have been reported. Furthermore, the biological properties of the target compounds, including their mutagenic, cytotoxic, enzymatic, anti- inflammatory and photosynthetic inhibitory activities have been summarized, paying particular attention on the compounds that have demonstrated antimicrobial properties via inhibition of quorum sensing and biofilm formation Keywords: Brominated 2(5H)-furanone derivatives, Regioselectivity, Marine natural products, Bioactivity, Antimicrobials, Quorum quenching Send Orders for Reprints to [email protected] Journal Name, Year, Volume 2 1. INTRODUCTION and conclusion: i) synthesis and bioactivity of 2(5H)- furanone derivatives with one bromine atom on the In the last four decades the chemistry of 2(5H)- heterocyclic ring; ii) synthesis and bioactivity of 2(5H)- furanones (also referred as 2-butenolides) has received furanone derivatives with two bromine atoms on the great interest and has experienced a remarkable expansion heterocyclic ring; iii) synthesis and bioactivity of 2(5H)- as evidenced by numeous reviews [1–18]. This interest is furanone derivatives possessing one bromine atom on the largely justified by the fact that these heterocycles include heterocyclic ring and monobrominated substituents; iv) biologically active natural compounds and substances synthesis and bioactivity of 2(5H)-furanone derivatives possessing interesting biological properties such as featuring one bromine atom on the heterocyclic ring and mutagenic, cytotoxic, anti-inflammatory, fungicidal and dibrominated substituents; v) synthesis and bioactivity of antibacterial activities. Furthermore, intense research has 2(5H)-furanone derivatives featuring two bromine atoms been conducted on the synthesis of brominated 2(5H)- on the heterocyclic ring and brominated substituents; vi) furanone derivatives as some compounds of this class have synthesis and bioactivity of 2(5H)-furanones with been found capable to block the bacterial quorum sensing monobrominated substituents; and vii) synthesis and (QS), i.e. the cell-to-cell communication of bacteria that bioactivity of 2(5H)-furanones with di-, tri- and tetra- include antibiotic resistant species [19,20], enhancing brominated substituents. bacterial clearance [21] and preventing swarming motility [22] and the production of QS-regulated virulence factors, The literature has been surveyed from 1951 until the notably biofilm formation [22–26]. end of February 2016. However, no updated review regarding a comprehensive description of the syntheses of natural and unnatural 2. SYNTHESES AND BIOACTIVITY OF 2(5H)- brominated 2(5H)-furanone derivatives and the biological FURANONE DERIVATIVES WITH ONE BROMINE properties associated to some of these heterocyclic ATOM ON THE HETEROCYCLIC RING compounds has been published so far. Only two reviews, which were published in 2004 and 2011 respectively, deal 2.1. SYNTHESIS AND BIOACTIVITY OF 3-BROMO- with the synthetic aspects of 3,4-dibromo-5-hydroxy- 2(5H)-FURANONE DERIVATIVES 2(5H)-furanone (mucobromic acid) (1) [10,14] and 3,4- In 1979, Reffstrup and Boll investigated the dibromo-2(5H)-furanone (2) (Figure 1)[14]. bromination reaction of 4-methoxy-2(5H)-furanone (3), a commercially available compound, and found that Br Br treatment of 3 with 1.0 equiv of NBS in CCl4 under reflux in the presence of catalytic amount of benzoyl peroxide gave a mixture of three brominated compounds which were Y O O easily separated and identified as 3-bromo-4-methoxy- 2(5H)-furanone (4), 5-bromo-4-methoxy-2(5H)-furanone 1 : Y = OH (mucobromic acid) 2 : Y = H (5) and 3,5-dibromo-4-methoxy-2(5H)-furanone (6) (Scheme 1) [27]. Compound 4, which was the main Figure 1. Structures of compounds 1 and 2 component of the mixture, was isolated in 45% yield [27]. This review with 263 references aims to provide a MeO thorough insight of the synthesis of 2(5H)-furanones with O bromine atoms on the heterocyclic ring and/or brominated O substituents that include natural products and unnatural 3 compounds used in the literature as versatile synthetic intermediates. The review also focuses on the biological NBS (1.0 equiv.) (PhCO)2O2 (cat.) properties of the synthesized compounds with particular CCl4, reflux, 1 h attention to those of the brominated compounds that have been found capable of interfering with the QS system of MeO Br MeO MeO Br bacteria, especially of those that are cause of mortality and morbidity in human beings. The literature data on these + + O Br O Br O topics have been organized on the basis of the structures of O O O the target compounds and have been subdivided in the 4 (45% yield) 5 (9% yield) 6 (5% yield) following sections interposed between the introduction XXX-XXX/14 $58.00+.00 © 2014 Bentham Science Publishers Title of the Article Journal Name, 2014, Vol. 0, No. 0 3 Scheme 1. Bromination of compound 3 furanone (9) in quantitative yield, which was acetalyzed with methanol providing compound 10 in high yield. The It is interesting to note that compound 5, which was subsequent bromine addition to 10 through a modified isolated in 9% yield, was used as direct precursor to the literature procedure [33], followed by pyridine-mediated in aglycone 7 (Figure 2) [27] of the antibiotic glycoside situ dehydrobromination of the resulting compound led to narthecide, which was isolated from Narthecium 11 in 65% yield [31]. ossifragrum [28]. In 2015, Zhao, Yang, Li and coworkers described that 3-bromo-2(5H)-furanone (13) could be obtained from MeO 2(5H)-furanone (12) in 47.6% yield by addition of bromine to 12 in Et2O under reflux, followed by Et3N-mediated HO O O dehydrobromination of the resulting adduct (Scheme 4)[34]. 7 Figure 2. Structure of aglycone 7 Br 1) Br2 (1.15 equiv.), Et2O, reflux, 4 h (in the dark) O 2) Et N (1.2 equiv.), 0 °C, 1 h In 2006, Heo and coworkers synthesized compound 4 in O 3 (47.6%) O 80% yield via addition of bromine to 3 and subsequent O 12 13 Et3N-mediated elimination of hydrobromic acid (Scheme 2) [29]. The synthesis was carried out according to a Scheme 4. Synthesis of 3-bromo-2(5H)-furanone (13) protocol described in the literature for the one-pot preparation of a-bromoenones from the corresponding Several years earlier, a similar procedure had been enones [30]. employed by de Echagüen and Ortuño for the synthesis of 3-bromo-5-methyl-2(5H)-furanone (15) from 5-methyl- MeO MeO Br Br2, CH2Cl2 2(5H)-furanone (14) (Scheme 5) [35]. However, in this 0 °C, 3 h case, CCl4 had been used in place of Et2O as the solvent for then Et3N, rt, 3 h O O the reaction with bromine. O (80%) O 3 4 Br Br2 (1.53 equiv.), CCl4 Scheme 2. High yielding synthesis of 3-bromo-4- reflux, 1.5 equiv. methoxy-2(5H)-furanone (4) O Me then Et3N (1,53 equiv.) O O Me rt, 2 h O (71%) In 2013, Vasamsetty, Khan and Mehta synthesized 3- 14 15 bromo-5-methoxy-2(5H)-furanone (11) via a four-step Br NBS (2.7 equiv.) protocol in which commercially available furfural (8) was Cp TiCl (19.5 equiv.) AIBN (cat), CCl4 2 2 the starting material (Scheme 3) [31]. reflux, 72 h Br Zn dust (3.1 equiv.) (63%) O O THF, rt, 0.5 h Br (71%) Rose Bengal (cat) 16 O MeOH, hν, O2 O (1O ) O OH 2 O Br H (quant.) 8 9 O O 1) PBr3 , Br2 0 °C, 20 min 17 MeOH then rt, 22 h Scheme 5. Synthesis of compounds 15 and 17 reflux, 3 d OMe 2) pyridine, 0 °C to rt O O (78%) 4 h (65%) 10 Compound 15 was then employed as the starting Br material for a two-step synthesis of 3-bromo-5-methylene- 2(5H)-furanone (17) involving the AIBN–mediated reaction of 15 with 2.7 equiv of NBS in CCl4 under reflux O OMe O and the reductive debromination of the resulting compound 11 16 by using zinc dust in THF in the presence of a catalytic amount of Cp2TiCl2 (Scheme 5) [35]. Scheme 3. Synthesis of 3-bromo-5-methoxy-2(5H)- In 1990, Sánchez-Ferrando and coworkers synthesized a furanone (11) 1 : 1 mixture of erythro- and threo-3-bromo-5-(1- hydroxyethyl)-2(5H)-furanone (21) in 20% yield by Thus, Rose Bengal sensitized photo-oxidation of 8 treatment of sorbic acid (18) with 2.62 equiv of NBS in according to the literature [32] gave 5-hydroxy-2(5H)- water at 37 °C for 18.5 h (Scheme 6) [36]. These authors 4 Journal Name, 2014, Vol. 0, No. 0 Principle Author et al. speculated that the formation of 21 could take place from O intermediates 19 and 20 (Scheme 6) [36]. N O + Me COOH Me3Si Me 18 24 25 (1.4 equiv.) (1.0 equiv.) NBS (2.62 equiv.) H O, 37 °C, 18.5 h 2 BF • Et O (1.4 equiv.) (20%) 3 2 NBS (3.2 equiv.), 0 °C, 20 min then aq.
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