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.
Keywords: Brominated 2(5H)-furanone derivatives, regioselectivity, marine natural products, bioactivity, antimicrobials, quorum quenching.
Current Organic Chemistry
Title:Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring and/or Brominated Substituents
Volume: 21 Issue: 11
Author(s): Renzo Rossi*, Marco Lessi, Chiara Manzini, Giulia Marianetti and Fabio Bellina*
Affiliation:
- Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Pisa,Italy
- Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Moruzzi 15, 56124 Pisa,Italy
Keywords: Brominated 2(5H)-furanone derivatives, regioselectivity, marine natural products, bioactivity, antimicrobials, quorum quenching.
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.
Export Options
About this article
Cite this article as:
Rossi Renzo*, Lessi Marco, Manzini Chiara, Marianetti Giulia and Bellina Fabio*, Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring and/or Brominated Substituents, Current Organic Chemistry 2017; 21 (11) . https://dx.doi.org/10.2174/1385272821666170111151917
DOI https://dx.doi.org/10.2174/1385272821666170111151917 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
Nitric Oxide and the Regulation of Apoptosis in Tumour Cells
Current Pharmaceutical Design EBI2, GPR18, and GPR17 – Three Structurally Related but Biologically Distinct 7TM Receptors
Current Topics in Medicinal Chemistry MYC-Mediated Synthetic Lethality for Treating Tumors
Current Cancer Drug Targets Heat Shock Proteins as Prognostic Markers of Cancer
Current Cancer Drug Targets Antisense Oligonucleotides in the Treatment of Cerebral Gliomas. Review of Concerning Patents
Recent Patents on CNS Drug Discovery (Discontinued) Interaction of ABC Multidrug Transporters with Anticancer Protein Kinase Inhibitors: Substrates and/or Inhibitors?
Current Cancer Drug Targets Current Adjuvant and Targeted Therapies for Pancreatic Adenocarcinoma
Current Medicinal Chemistry Targeting Epigenome As An Innovative Pharmacological Strategy For Castration-resistant Prostate Cancer
Clinical Cancer Drugs Ex Vivo Models of HIV Sexual Transmission and Microbicide Development
Current HIV Research Lipid-Protamine-DNA-Mediated Antigen Delivery
Current Drug Delivery Xenobiotic-Induced Transcriptional Regulation of Xenobiotic Metabolizing Enzymes of the Cytochrome P450 Superfamily in Human Extrahepatic Tissues
Current Drug Metabolism Tumor-Induced Metabolism and T Cells Located in Tumor Environment
Current Cancer Drug Targets Potential of Taming MicroRNA on Driver Seat to Control Mitochondrial Horses in Breast Carcinoma
MicroRNA Mechanisms Involved in the Protective Effects of Metformin Against Nonalcoholic Fatty Liver Disease
Current Medicinal Chemistry Synthesis, Molecular Docking, and 2D-QSAR Modeling of Quinoxaline Derivatives as Potent Anticancer Agents against Triple-negative Breast Cancer
Current Topics in Medicinal Chemistry GPR55 and its Interaction with Membrane Lipids: Comparison with Other Endocannabinoid-Binding Receptors
Current Medicinal Chemistry The Role of 3D Pharmacophore Mapping Based Virtual Screening for Identification of Novel Anticancer Agents: An Overview
Current Topics in Medicinal Chemistry 4-Aryl-4H-Chromene-3-Carbonitrile Derivatives: Evaluation of Src Kinase Inhibitory and Anticancer Activities
Medicinal Chemistry Current Issues in the Utility of Blood Oxygen Level Dependent MRI for the Assessment of Modulations in Tumor Oxygenation
Current Medical Imaging The Roles of Parathyroid Hormone and Calcitonin in Bone Remodeling: Prospects for Novel Therapeutics
Endocrine, Metabolic & Immune Disorders - Drug Targets