766-38-1

Usage

Uses

Used in Periodontal Disease Applications:
3,4-dibromo-5-hydroxyfuran-2(5H)-one is used as a periodontal disease marker for disease drug screening. Its presence can indicate the presence of periodontal disease, allowing for targeted treatment and monitoring of the condition.
Used in Anticancer Applications:
3,4-dibromo-5-hydroxyfuran-2(5H)-one is used as an anti-cancer agent, potentially targeting and inhibiting the growth of cancer cells. Its specific mechanism of action and effectiveness in various types of cancer may vary and require further research and clinical trials.
Used in Infectious Disease Applications:
3,4-dibromo-5-hydroxyfuran-2(5H)-one is used as an autoinducer 2 inhibitor and/or therapeutic agent for infectious diseases. By inhibiting the quorum sensing mechanism in bacteria, it can potentially reduce the virulence of pathogens and help in the treatment of various infections.

InChI:InChI=1/C4H2Br2O3/c5-1-2(6)4(8)9-3(1)7/h3,7H

Upstream product

• 124786-35-2 dibromo-malaldehyde 
• 98-01-1 furfural 
• 88-14-2 2-furanoic acid 
• 914362-04-2 3,4-dibromo-5-[(2-methoxyethoxy)methoxy]-5H-furan-2-one 

Downstream Products

• 20030-12-0 3,4-dibromo-5-(2-oxo-2-phenethyl)-5H-furan-2-one 
• 4595-59-9 5-bromopyrimidine 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 85575-99-1 ethyl (2E)-5-bromo-2-penten-4-ynoate 
• 85575-98-0 ethyl (2E,4Z)-4,5-dibromo-2,4-pentadienoate 
• 92576-92-6 4-(3',4'-dimethoxyphenyl)-2,3-dibromocrotonolactone 
• 4499-39-2 4-(4'-methoxyphenyl)-2,3-dibromocrotonolactone 
• 149418-41-7 3,4-dibromo-2(5H)-furanone 
• 21958-21-4 3,4-dibromo-5-(2,4,6-trimethoxy-phenyl)-5H-furan-2-one 
• 21958-20-3 3,4-dibromo-5-(2,3,4-trimethoxy-phenyl)-5H-furan-2-one 
• 27314-17-6 4,5-dibromo-2-(3-trifluoromethyl-phenyl)-2H-pyridazin-3-one 
• 14305-08-9 4,5-dibromo-2-phenylpyridazin-3(2H)-one 
• 21958-19-0 3,4-dibromo-5-(2,4-dimethoxy-phenyl)-5H-furan-2-one 
• 221031-08-9 4,5-dibromo-2-(3,4-difluorophenyl)-2H-pyridazin-3-one 

Relevant academic research and scientific papers

Design, synthesis and evaluation of halogenated furanone derivatives as quorum sensing inhibitors in Pseudomonas aeruginosa

The biofilm formation of Pseudomonas aeruginosa (P. aeruginosa) is regulated by a phenomenon of quorum sensing (QS). With 5-hydroxyl-3,4-halogenated-5H-furan-2-ones as beginning, analogs bearing alkyl chains, vinyl bromide, or aromatic rings were designed and synthesized. The minimum inhibitory concentration (MIC) of the compounds against P. aeruginosa was assayed and the biofilm inhibition ratio was determined at different concentrations lower than the MIC. C-5 aromatic substituted furanones showed remarkable biofilm formation as well as inhibition of virulence factor production in P. aeruginosa. Fluorescence report analysis identified the QS regulatory mechanism of the most active compound 29. This study provides us a novel candidate for combating drug resistant bacteria strains by merely inhibiting biofilm formation. Without suppressing the regular life cycle of the bacteria, bacterial resistance mechanisms may not be activated.

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.]

Synthesis and biological activities of dithiocarbamates containing 2(5H)-furanone-piperazine

A series of new dithiocarbamates containing a 2(5H)-furanone-piperazine group was synthesized. These compounds show good in vitro cytoxic activity. Among them, compound 6c exhibits the best inhibitory activity against HeLa cell lines with an IC50 of 0.06 ± 0.01 μM for 72 h, and it has good inhibitory activity against SMMC-7721 cell lines with an IC50 of 0.006 ± 0.04 μM for 72 h, but the toxicity was lower against LO2 cell lines with an IC50 of 45.76 ± 0.01 μM. The result showed that compound 6c is far more cytoxic towards cancer cell lines than towards benign cell lines compared with cytosine arabinoside (ARA) in vitro.

Bromofuranone ester compound and preparation method and application thereof

The invention discloses a bromofuranone ester compound and a preparation method and application of the bromofuranone ester compound. The bromofuranone ester compound is applied to preparation of a medicament for treating diabetic foot drug-resistant bacterial infection, and used as an active constituent and pharmaceutically acceptable excipient. The preparation method of the bromofuranone ester compound comprises the following steps: (1) adding a compound I as shown in the formula I to a low-temperature solvent, stirring, dropwise adding bromine slowly, rising the temperature and carrying outa reflux reaction, stopping to react, cooling, performing suction filtration after solids are precipitated, washing a filter cake with a reducing solution and water, and purifying to obtain a compoundII as shown in the formula II; (2) adding the compound II to the solvent, sequentially adding a compound III, a dehydrant and a catalyst, introducing nitrogen, stirring at room temperature and reacting, and carrying out post-processing and purifying to obtain a compound IV as shown in the formula IV.

Design and synthesis of 2(5H)-furanone liquid-crystal compounds based on natural molecules and biphenyl derivatives

Starting from natural molecules, for example l-menthol and amino acids, a series of 2(5H)-furanone liquid-crystal compounds were designed, and synthesized by esterification of N-[5-menthoxy-2(5H)-furanonyl] amino acids with biphenyl-4-ol or biphenyl-4,4′-diol in the presence of dehydrating agents. The structures of all the novel compounds were confirmed by FTIR, 1H NMR, and mass spectroscopy, and by elemental analysis. The liquid-crystal properties of the target compounds were characterized by differential scanning calorimetry (DSC), X-ray diffraction (XRD), and polarization optical microscopy (POM). The DSC and XRD results showed that some compounds containing short alkyl chains or with the phenyl far from the amino in the amino acid unit formed a mesomorphic phase. Products obtained from biphenyl-4,4′-diol were more likely to form a mesomorphic phase. However, POM revealed no optical texture. These investigations provide, for the first time, a basis for application of 2(5H)-furanones in liquid crystals by combination of different functional units, including biphenyl, l-menthol, and amino acids.

Synthesis of 3-bromotetronamides via amination of 3,4-dibromofuran-2(5H)- one

This work describes the direct synthesis of 3-bromotetronamides in good yields through the reaction of 3,4-dibromofuran-2(5H)-one, obtained from furfural, with primary and secondary amines. Aromatic amines were more tolerated than aliphatic and heteroaromatic ones. The X-ray structures of five derivatives are described.

Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing γ-butenolide moiety and preliminary evaluation of in vitro anticancer activity

A new series of chiral 1,3,4-thiadiazoles derivatives possessing γ-substituted butenolide moiety were synthesized and evaluated for in vitro anticancer properties. All the compounds showed good anticancer activities against Hela cell lines. Of all the studied compounds, compound 9e exhibited the best inhibitory activity with an IC50 of 0.9 μM. After being treated with 0.1 μg/mL compound 9e for 24 h, the growth inhibition rate of Hela cell lines was 59.2%.

Regioselective entry to bromo-γ-hydroxybutenolides: Useful building blocks for assemblying natural product-like libraries

(Chemical Equation Presented) We report a regioselective entry to 3-bromo- and 4-bromo-5-hydroxy-5H-furan-2-ones by photooxidation of 3-bromofuran with a singlet oxygen in the presence of a suitable base. By this procedure, a variety of 3-substituted γ-hydroxybutenolides have become for the first time easily accessible. Strategies employing these highly functionalized building blocks for the preparation of focused libraries of natural-like molecules are also discussed.