32323-47-0

Upstream product

• 1775-46-8 3,5-dibromolevulinic acid 
• 62557-43-1 3-bromolevulinic acid 
• 14594-23-1 5-bromolaevulinic 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

• 676556-27-7 (Z)-4-bromo-5-(trans-3-phenyl-2-propenylidene)-2(5H)-furanone 
• 676556-29-9 (Z)-4-bromo-5-(phenylmethylene)furan-2-(5H)-one 
• 1218769-64-2 4-phenyl-(Z)-5-(thiophene-3-ylmethylene)furan-2-(5H)-one 
• 935471-87-7 4-bromo-5-bromomethyl-5-hydroxy-1-phenyl-1,5-dihydro-pyrrol-2-one 
• 664336-37-2 4-bromo-5-benzylamino-5-bromomethyl-2(5H)furanone 
• 664336-30-5 4-bromo-5-phenylaminomethylene-2(5H)-furanone 
• 385438-39-1 4-phenyl-5-bromomethylene-2-(5H)-furanone 
• 216227-78-0 4-(4-methoxyphenyl)-5-[(Z)-(4-methoxyphenyl)methylidene]furan-2-one 

Relevant academic research and scientific papers

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.]

Design and synthesis of aryl-substituted pyrrolidone derivatives as quorum sensing inhibitors

Quorum sensing, a common cell-to-cell communication system, is considered to have promising application in antibacterial therapy since they are expected to induce lower bacterial resistance than conventional antibiotics. However, most of present quorum sensing inhibitors have potent cell toxicity, which limits their application. In this study we evaluated the diverse quorum sensing inhibition activities of different biaromatic furanones and brominated pyrrolones. On this basis, we further designed and synthesized a new series of aryl-substituted pyrrolones 12a-12f. In the quorum sensing inhibition assay, compound 12a showed improved characteristics and low toxicity against human hepatocellular carcinoma cell. In particular, it can inhibit the pyocyanin production and protease activity of Pseudomonas aeruginosa by 80.6 and 78.5%, respectively. Besides, in this series, some compounds exerted moderate biofilm inhibition activity. To sum up, all the findings indicate that aryl-substituted pyrrolidone derivatives are worth further investigation as quorum sensing inhibitors.

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

METHYLENE FURANONE DERIVATIVES AND USE OF SAID DERIVATIVES AS A PHOTOPROTECTING OR ANTIOXIDANT OR DEPIGMENTATION AGENT IN COSMETIC OR DERMATOLOGICAL COMPOSITIONS

The present invention relates to novel methylene furanone derivatives as well as the use thereof as a protective, antioxidant, or depigmentation agent in cosmetic or dermatological compositions. The invention also relates to a method for preparing said derivatives involving a Suzuki-Miyaura coupling reaction from corresponding dibromofuranone derivatives. The invention also relates to a method of preparation involving a coupling reaction of 2-methoxy-furan derivatives with a ketone followed by dehydration.

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

A Novel Access to γ-Alkylidenebutenolides: Sequential Stille Couplings of Dibromomethylenebutenolides

γ-(Dibromomethylene)butenolide (2) and β-bromo-γ- (bromomethylene)butenolide (Z-5), both of which obtained from dibromolevulinic acid (6) in a single step, underwent Pd-catalyzed couplings with phenyl- or styryltributylstannane giving mono-bromobutenolides with excellent stereo- and regiocontrol. A second Stille coupling or the reduction with Zn dust led to bromine-free γ-alkylidenebutenolides as single stereoisomers.

Synthesis of cyclic compounds

A method for the preparation of a compound of formula (II) wherein R1 and R2 are independently H, alkyl, alkoxy, oxoalkyl, alkenyl, aryl or arylalkyl whether unsubstituted or substituted, optionally interrupted by one or more hetero atoms, straight chain or branched chain, hydrophilic, hydrophobic or fluorophilic; R3, R4, R5 and R6 are independently or all hydrogen or halogen; provided that at least two of the R3, R4, R5 and R6 are halogens.

Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones

A synthesis of ethyl-, butyl-, hexyl- and dodecyl-substituted fimbrolides from alkyl-substituted levulinic acid derivatives through bromination and acid promoted lactonisation is described. The underlying reactions have been investigated using levulinic acid as a model, and the effects of varying the bromination conditions and changing acid concentration on product distribution are discussed. Dibromination proceeds best in CHCl3 and proceeds in EtOH-free CHCl3 without the complication of ester formation. Cyclisation. occurs with concomitant oxidation in 98-100% H2SO4 but gives highest yields of fimbrolides in 100% H2SO4. The formation of related beckerelide substances is also described.