Brominated analogs of 3‐chloro‐4‐(dichloromethyl)‐5‐hydroxy‐2(5<i>H</i>)‐furanone: Preparation of 3‐chloro‐4‐(bromochloromethyl)‐5‐hydroxy‐2(5<i>H</i>)‐furanone and mutagenicity studies

Ramos, Isabel; Lloveras, Maia; Soláns, Xavier; Huici, Alicia; Messeguer, Ángel

doi:10.1002/etc.5620191103

Cited by 8 publications

(5 citation statements)

References 25 publications

(36 reference statements)

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“…Not all of the currently identified signal interference molecules could be used practically; toxicity analysis and in vivo efficacy evaluation might significantly narrow down the potential candidates. For example, halogenated furanones are generally very reactive and several tested derivatives were found mutagenic (Ramos et al ., 2000), which raises the concern of using this group of compounds in medicine and industries (Hentzer and Givskov, 2003). However, unlike the antibiotic‐like candidates, which have been screened and characterized extensively for more than a half century, potential signal interference molecules in natural systems and in synthetic chemical libraries have rarely been touched and screening of novel interference compounds may prove productive.…”

Section: Signal Interference and Infection Controlmentioning

confidence: 99%

Quorum sensing and signal interference: diverse implications

Zhang¹,

Dong²

2004

Molecular Microbiology

267

155

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SummaryQuorum sensing (QS) is a community genetic regulation mechanism that controls microbiological functions of medical, agricultural and industrial importance. Discovery of microbial QS signals and the signalling mechanisms led to identification of numerous enzymatic and non-enzymatic signal interference mechanisms that quench microbial QS signalling. Evidence is accumulating that such signal interference mechanisms can be developed as promising approaches to control microbial infection and biofilm formation. In addition, these mechanisms exist not only in microorganisms but also in the host organisms of bacterial pathogens, highlighting their potential implications in microbial ecology and in host-pathogen interactions. Investigation of QS and signal interference mechanisms might significantly broaden the scope of research in microbiology.

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Section: Signal Interference and Infection Controlmentioning

confidence: 99%

Quorum sensing and signal interference: diverse implications

Zhang¹,

Dong²

2004

Molecular Microbiology

267

155

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“…In 2000, 4-(bromochloromethyl)-3-chloro-5-hydroxy-2(5H)-furanone (297) (BMX-1) and 3-chloro-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone (298) (BMX-2) were synthesized by Messeguer and coworkers from methyl-3-methyl-2-butenoate (265a) using the reaction sequence outlined in Scheme 103 [183,189]. the E-and Z-stereoisomers were in a 1.8 : 1 ratio.…”

Section: Scheme 102 Synthesis Of 5-(1-bromoethyl)-2(5h)furanone (294)mentioning

confidence: 99%

“…This mixture was subjected to allylic bromination with an excess of NBS in the presence of light at 110 °C producing a mixture of (E)-and (Z)-296 in a 1 : 1 ratio and in only 18% yield. Finally, hydrolysis and subsequent cyclization of this mixture by treatment with 70% methanesulfonic acid at 140 °C gave a mixture of compounds 297 (BMX-1) and 298 (BMX-2) from which pure compounds 297 and 298 were isolated in 25% and 20% yield, respectively, via reversed phase HPLC [183,189].…”

Section: Scheme 102 Synthesis Of 5-(1-bromoethyl)-2(5h)furanone (294)mentioning

confidence: 99%

Section: Scheme 102 Synthesis Of 5-(1-bromoethyl)-2(5h)furanone (294)mentioning

confidence: 99%

“…In 2000, Messeguer and coworkers evaluated the mutagenic activity of compounds BMX-1, BMX-2 and BMX-3 by employing the Ames test with Salmonella typhimurium strain TA98 and TA100 and found that the mutagenic potencies in TA100 without S9 metabolic activation were 22.05 ± 3.15 revertants/ng for BMX-1 (297), 28.64 ± 2.65 revertants/ng for BMX-2 (298) and 37.29 ± 5.73 revertants/ng for BMX-3 (299) [189]. Notably, the mutagenic potencies proved to be six-to-nine fold lower in the TA98 strain without metabolic activation [189]. The stereo-and regioselective synthesis of 304 began with the Suzuki-Miyaura cross-coupling reaction of 3,4dichloro-2(5H)-furanone (300) with 1.1 equiv of arylboronic acid 301 in the presence of KF as the base, a Pd 2 (dba) 3 /P(o-Tol) 3 catalyst system and using toluene as solvent, which gave compound 302 in 61% yield.…”

Section: Scheme 102 Synthesis Of 5-(1-bromoethyl)-2(5h)furanone (294)mentioning

confidence: 99%

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

Rossi

Lessi

Manzini

et al. 2017

COC

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This review 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 six classes of brominated furanone derivatives that were synthesized: i) 2(5H)-furanone derivatives with one bromine atom on the heterocyclic ring; ii) 2(5H)-furanone derivatives with two bromine atoms on the heterocyclic ring; iii) 2(5H)-furanone derivatives featuring one bromine atom on the heterocyclic ring and monobrominated substituents; iv) 2(5H)- furanone derivatives featuring one bromine atom on the heterocyclic ring and dibrominated substituents; v) 2(5H)-furanone derivatives with monobrominated substituents; and vi) 2(5H)-furanones featuring dibrominated substituents. 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

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