247167-54-0

Basic information

• Product Name: (Z-)-4-BroMo-5-(broMoMethylene)-2(5H)-furanone
• Synonyms: (Z-)-4-BroMo-5-(broMoMethylene)-2(5H)-furanone;Furanone C-30;(Z-)-4-BROMO-5-(BROMOMETHYLENE)-2(5H;2(5H)-Furanone, 4-bromo-5-(bromomethylene)-, (5Z)-
• CAS NO: 247167-54-0
• Molecular Formula: C5H2Br2O2
• Molecular Weight: 253.87618
• EINECS: -0
• Mol File: 247167-54-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 97-99 °C
• Boiling Point: 205.9±40.0 °C(Predicted)
• Appearance: /
• Density: 2.650±0.06 g/cm3(Predicted)
• Storage Temp.: ?20°C
• BRN: 120928
• CAS DataBase Reference: (Z-)-4-BroMo-5-(broMoMethylene)-2(5H)-furanone(CAS DataBase Reference)
• NIST Chemistry Reference: (Z-)-4-BroMo-5-(broMoMethylene)-2(5H)-furanone(247167-54-0)
• EPA Substance Registry System: (Z-)-4-BroMo-5-(broMoMethylene)-2(5H)-furanone(247167-54-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 247167-54-0(Hazardous Substances Data)

Usage

Biochem/physiol Actions

The synthetic furanones C30 interfered with the actions of acyl-HSL molecules and inhibited gene expression regulated by quorum-sensing systems in P. aeruginosa.

Upstream product

• 62557-43-1 3-bromolevulinic acid 
• 14594-23-1 5-bromolaevulinic acid 
• 1775-46-8 3,5-dibromolevulinic acid 
• 123-76-2 levulinic acid 
• 385438-58-4 2,3-dibromo-4-oxo-valeric acid 
• 385438-64-2 2,3,5-tribromo-4-oxopentanoic acid 

Downstream Products

• 216227-78-0 4-(4-methoxyphenyl)-5-[(Z)-(4-methoxyphenyl)methylidene]furan-2-one 

Relevant articles and documents

Synthesis and cytotoxic evaluation of halogenated furanones

Abstract: The objective of the current study is to evaluate the potency of halogen-furan-2(5H)-one-type derivatives against human cancer cell lines. Four known bromofuran-2(5H)-one-type derivatives, as well as five new and two known bromo-4-(phenylamino)furan-2(5H)-one-type compounds and six novel and two known halogen-4-alkyl-5-phenyl-3-(phenylamino)furan-2(5H)-one-type derivatives, were synthesized and evaluated for their anticancer activity against prostate (PC-3) and colon (HCT-116) human cancer cell lines. The results showed that only the bromofuran-2(5H)-ones were cytotoxic in both cell lines. Three of these displayed particularly useful antiproliferative activities, in both cancer cells evaluated. (E)-5-(Bromomethylene)furan-2-(5H)-one was the most active against PC-3 (IC50 0.93 ± 0.02?μM) while 3,4-dibromofuran-2(5H)-one was the most active against HCT-116 (IC50 0.4 ± 0.04?μM). Furthermore, flow cytometry studies revealed that the bromofuran-2(5H)-ones induced cell death by apoptosis. Also, it was found that the cytotoxic furanones induced lipid peroxidation, determined by TBARS assay. Thus, cytotoxicity of the active compounds could be associated with ROS production. Additionally, it must be taken into account that all cytotoxic compounds contain an electrophilic carbon atom in position 4, which can explain, through a non-specific reactivity with nucleophiles, the cytotoxic activity of these compounds. Graphic abstract: [Figure not available: see fulltext.]

Bacterial quorum sensing inhibitors as well as preparation method and application thereof

The invention provides bacterial quorum sensing inhibitors as well as a preparation method and an application thereof, and belongs to the technical field of medical chemistry. The bacterial quorum sensing inhibitors mainly comprise alpha-pyridoin derivati

Structure-activity relationship of brominated 3-alkyl-5-methylene-2(5H)- furanones and alkylmaleic anhydrides as inhibitors of Salmonella biofilm formation and quorum sensing regulated bioluminescence in Vibrio harveyi

A library of 25 1′-unsubstituted and 1′-bromo or 1′-acetoxy 3-alkyl-5-methylene-2(5H)-furanones and two 3-alkylmaleic anhydrides was synthesized using existing and new methods. This library was tested for the antagonistic effect against the biofilm format