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

Abstract

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

Bis‐2(5H)‐furanone derivatives as new anticancer agents: Design, synthesis, biological evaluation, and mechanism studies

“…Due to good reactivity and biological activity of 2(5 H )‐furanone compounds, the design and synthesis of 2(5 H )‐furanone‐based drugs have attracted chemist's research interests . In our previous research, we reported a series of 4‐benzidino‐2(5 H )‐furanones 3 (Scheme 1) with acceptable antiproliferative activity against breast cancer cell [15c].…”

“…2(5 H )‐Furanone is present in a large number of biologically active compounds, including natural products and pharmaceutical agents . In the field of medicinal chemistry, halogenated 2(5 H )‐furanone derivatives have always received considerable attention because of their biological importance and synthetic feasibility . In particular, 4‐arylamino‐2(5 H )‐furanone scaffold is considered as an important template for the development of new drugs .…”

Heterocyclic Chemistry Applied to the Design of N-Acyl Homoserine Lactone Analogues as Bacterial Quorum Sensing Signals Mimics

“…For example, the natural ( Z )-4-bromo-5(bromomethylene)-2( 5H )-furanone-C30 has been extensively studied and recent studies showed that this compound is able to bind to LuxR type protein such as LasR and RhlR in pseudomonas aeruginosa [ 57 ]. In 2017, Fabio Bellina and co-workers described a state of the art of the chemistry of furanones and their relevant bioactivity [ 58 ]. Below we give an update on the furanone type compounds with examples reported since, and with compounds with similar structures.…”

Effects of ZnCl2 on the distribution of aldehydes and ketones in bio-oils from catalytic pyrolysis of different biomass

“…2(5H)-furanone ($18/g, purity: 98%, 2019) has high biological activities; hence, it is widely used for antibacterial, anti-inflammatory, antiviral, and anti-cancer applications. In addition, 2(5H)-furanone has been shown to be a suitable starting point to synthesize medicinal and industrial products in recent years (Li et al 2016;Rossi et al 2017).…”