20005-42-9

Usage

Uses

Used in Chemical Synthesis:
5-(4-Bromophenyl)furfural is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure with a bromine atom attached to a phenyl group and a furan ring makes it a valuable building block in the creation of complex molecules for pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-(4-Bromophenyl)furfural is used as a key component in the development of new drugs. Its ability to be oxidized to γ-keto carboxylic acid can be exploited in the synthesis of novel drug candidates with potential therapeutic applications.
Used in Material Science:
5-(4-Bromophenyl)furfural can be utilized in the field of material science for the development of new materials with specific properties. Its aromatic and bromine-containing structure may contribute to the creation of materials with enhanced stability, reactivity, or other desirable characteristics.
Used in Dye and Pigment Industry:
The brown powder form of 5-(4-Bromophenyl)furfural suggests its potential use in the dye and pigment industry. It could be employed as a colorant or as a starting material for the synthesis of more complex dyes and pigments with specific color properties.
Used in Analytical Chemistry:
Due to its distinct chemical properties, 5-(4-Bromophenyl)furfural may find applications in analytical chemistry as a reagent or a reference compound for the development of new analytical methods or the calibration of existing ones. Its bromine content and furan ring could be particularly useful in this context.

InChI:InChI=1/C11H7BrO2/c12-9-3-1-8(2-4-9)11-6-5-10(7-13)14-11/h1-7H

Upstream product

• 98-01-1 furfural 
• 106-40-1 4-bromo-aniline 
• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 5467-74-3 4-Bromophenylboronic acid 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 2028-85-5 (4-bromophenyl)diazonium chloride 
• 75-61-6 dibromodifluoromethane 
• 857048-92-1 2-(4-bromophenyl)-5-[(prop-2-yn-1-yloxy)methyl]furan 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 589-87-7 1,4-bromoiodobenzene 
• 1276045-68-1 5-(1,3-dioxolan-2-yl)-2-furanylzinc bromide 
• 27329-70-0 5-formylfurane-2-boronic acid 
• 106-37-6 1.4-dibromobenzene 
• 32529-50-3 2-(4-bromo-2-furanyl)-1,3-dioxolane 

Downstream Products

• 35274-39-6 5-[5-(4-bromo-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one 
• 41939-41-7 2-(5-(4-bromophenyl)furan-2-yl)-1H-benzo[d]imidazole 
• 41939-52-0 2-[5-(4-bromo-phenyl)-furan-2-yl]-1-methyl-5-nitro-1H-benzoimidazole 
• 139267-94-0 4-<5-(4-p-Bromophenyl)-2-furfurylidene>amino-3-mercapto-5-p-chlorophenyl-1,2,4-triazole 
• 139267-91-7 4-<5-(4-p-Bromophenyl)-2-furfurylidene>amino-3-mercapto-5-propyl-1,2,4-triazole 
• 139267-92-8 4-<5-(4-p-Bromophenyl)-2-furfurylidene>amino-3-mercapto-5-phenyl-1,2,4-triazole 
• 58110-40-0 3-[5-(4-bromo-phenyl)-furan-2-yl]-acrylic acid 
• 139267-89-3 4-{[1-[5-(4-Bromo-phenyl)-furan-2-yl]-meth-(Z)-ylidene]-amino}-5-methyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 139267-90-6 4-{[1-[5-(4-Bromo-phenyl)-furan-2-yl]-meth-(Z)-ylidene]-amino}-5-ethyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 269740-03-6 C₂₆H₂₀Br₂N₄O₄ 
• 20005-40-7 3-[5-(4-bromo-phenyl)-furan-2-yl]-1-phenyl-propenone 
• 294635-96-4 (E)-3-[5-(4-Bromo-phenyl)-furan-2-yl]-1-(4-methoxy-phenyl)-propenone 

Relevant academic research and scientific papers

Synthesis of novel diarylpyrrole-2-carbaldehydes by ring transformations

Various diarylpyrrole-2-carbaldehydes were prepared by ring transformation of arylfuran-2-carbaldehydes with anilines in the presence of an acid. The synthesized compounds were characterized through elemental analysis and spectroscopic techniques (FTIR, 1H NMR, 13C NMR and mass spectra).

Synthesis of arylfuran derivatives as potential antibacterial agents

Bacterial infections represent a serious health care problem mainly due to the misuse and overuse of antibiotics, with consequent emergence of multidrug resistant bacterial strains. Then, because the urgent need to find novel and alternative antibacterial agents, the present work focuses on the synthesis of arylfuran derivatives with potential antimicrobial activity. Eighteen arylfuran derivatives were synthesized and evaluated for their antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Among them, seven compounds containing an amino group in their structure showed activity, with compound 24 being the most effective against both Gram-negative (E. coli, MIC = 49 μM) and Gram-positive (S. aureus, MIC = 98 μM) bacteria, besides having exhibited a modest activity against P. aeruginosa (MIC = 770 μM). In addition, based on in silico studies, this is a druglike compound since it does not violate any rules for predicting oral bioavailability. In this context, the significant antibacterial potential and the low similarity with known antibiotics indicate the innovative aspect of compound 24.

5-Aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety as potential PTP1B inhibitors

Two series of 5-aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, 5g was found to have the best PTP1B inhibitory potency (IC50 = 2.66 ± 0.16 μM) and the best cell division cycle 25 homolog B (CDC25B) inhibitory potency (IC50 = 0.25 ± 0.02 μM). Enzymatic data together with molecular modeling results demonstrated that the introduction of a sec-butyl group at the 2-position of the carboxyl group remarkably improved the PTP1B inhibitory activity.

Synthesis of novel benzimidazoles and benzothiazoles via furan-2-carboxaldehydes, o-phenylenediamines, and 2-aminothiophenol using Cu(II) Schiff-base@SiO2 as a nanocatalyst

2-(5-Substituted phenyl)furan-2-carboxaldehyde derivatives were prepared by using an efficient copper(II) complex of tetradentate Schiff-base ligand immobilized onto silica as a heterogeneous nanocatalyst [Cu(II) Schiff-base@SiO2] (5.0?mol%) using anilines, sodium nitrite, and furan-2-carboxaldehyde. Furthermore, attractive di-heteroaryl benzo-fused systems such as benzimidazole and benzothiazole derivatives were synthesized using this nanocatalyst (5.0?mol%) via the reaction of o-phenylenediamines and 2-aminothiophenol with 2-(5-substituted phenyl)furan-2-carboxaldehydes in EtOH. The catalyst was characterized by Fourier transform infrared (FT-IR), field emission scanning electron microscope (FESEM), energy-dispersive X-ray spectroscopy (EDX), X-ray powder diffraction (XRD), and inductively coupled plasma (ICP) techniques. The advantages of the present catalytic system are short reaction times, mild conditions, good to excellent yields, and low amount of nanocatalyst. Moreover, to the best of our knowledge, this is the first time of using the same catalyst in two steps including synthesis of 2-(5-substituted phenyl)furan-2-carboxaldehyde and benzimidazole or benzothiazole derivatives. In addition, the synthesized catalyst was recycled very well and reused several times without significant loss of its catalytic activity.

Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy

Serine, the source of the one-carbon units essential for de novo purine and deoxythymidine synthesis plays a crucial role in the growth of cancer cells. Phosphoglycerate dehydrogenase (PHGDH) which catalyzes the first, rate-limiting step in de novo serine biosynthesis has become a promising target for the cancer treatment. Here we identified H-G6 as a potential PHGDH inhibitor from the screening of an in-house small molecule library based on the enzymatic assay. We adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest. Collectively, our results suggest that b36 is a novel PHGDH inhibitor, which could be a promising modulator to reprogram the serine synthesis pathway and might be a potential anticancer lead worth further exploration.

Discovery of (5-Phenylfuran-2-yl)Methanamine derivatives as new human sirtuin 2 Inhibitors

Human sirtuin 2 (SIRT2), a member of the sirtuin family, has been considered as a promising drug target in cancer, neurodegenerative diseases, type II diabetes, and bacterial infections. Thus, SIRT2 inhibitors have been involved in effective treatment strategies for related diseases. Using previously established fluorescence-based assays for SIRT2 activity tests, the authors screened their in-house database and identified a compound, 4-(5-((3-(quinolin-5-yl)ureido)methyl) furan-2-yl)benzoic acid (20), which displayed 63 ± 5% and 35 ± 3% inhibition against SIRT2 at 100 μM and 10 μM, respectively. The structure-activity relationship (SAR) analyses of a series of synthesized (5-phenylfuran-2-yl)methanamine derivatives led to the identification of a potent compound 25 with an IC50 value of 2.47 μM, which is more potent than AGK2 (IC50 = 17.75 μM). Meanwhile, 25 likely possesses better water solubility (cLogP = 1.63 and cLogS = ?3.63). Finally, the molecular docking analyses indicated that 25 fitted well with the induced hydrophobic pocket of SIRT2.

5-Aryl-2-furaldehydes in the synthesis of tetrahydropyrimidinones by Biginelli reaction

5-Aryl-2-furaldehydes, obtained by furfural arylation with arenediazonium salts, react with ethyl acetoacetate or acetylacetone and (thio)- urea in the presence of FeCl3·6H2O as a catalyst. A series of ethyl 4-(5-aryl-2-furyl)-6-methyl-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine- 5-carboxylates was obtained.

Antimalarial agents against both sexual and asexual parasites stages: structure-activity relationships and biological studies of the Malaria Box compound 1-[5-(4-bromo-2-chlorophenyl)furan-2-yl]-N-[(piperidin-4-yl)methyl]methanamine (MMV019918) and analogues

Therapies addressing multiple stages of Plasmodium falciparum life cycle are highly desirable for implementing malaria elimination strategies. MMV019918 (1, 1-[5-(4-bromo-2-chlorophenyl)furan-2-yl]-N-[(piperidin-4-yl)methyl]methanamine) was selected from the MMV Malaria Box for its dual activity against both asexual stages and gametocytes. In-depth structure-activity relationship studies and cytotoxicity evaluation led to the selection of 25 for further biological investigation. The potential transmission blocking activity of 25 versus P. falciparum was confirmed through the standard membrane-feeding assay. Both 1 and 25 significantly prolonged atrioventricular conduction time in Langendorff-isolated rat hearts, and showed inhibitory activity of Ba2+ current through Cav1.2 channels. An in silico target-fishing study suggested the enzyme phosphoethanolamine methyltransferase (PfPMT) as a potential target. However, compound activity against PfPMT did not track with the antiplasmodial activity, suggesting the latter activity relies on a different molecular target. Nevertheless, 25 showed interesting activity against PfPMT, which could be an important starting point for the identification of more potent inhibitors active against both sexual and asexual stages of the parasite.

Access to Densely Functionalized Chalcone Derivatives with a 2-Pyridone Subunit via Pd/Cu-Catalyzed Oxidative Furan-Yne Cyclization of N -(2-Furanylmethyl) Alkynamides under Air

A protocol for synthesis of chalcone derivatives with a 2-pyridone subunit from N-(2-furanylmethyl) alkynamides is reported. This synthesis involves Pd/Cu-catalyzed oxidative furan-yne cyclization at room temperature in air and may proceed via nucleopalladation of the alkyne to form a vinylpalladium intermediate, with a furan ring acting as the nucleophile.

Covalently Immobilized Lipases are Efficient Stereoselective Catalysts for the Kinetic Resolution of rac-(5-Phenylfuran-2-yl)-β-alanine Ethyl Ester Hydrochlorides

Lipase-catalyzed enzymatic resolution of several new, exotic and variously substituted rac-(5-phenylfuran-2-yl)-β-alanine ethyl esters was investigated. Given the structural instability of unsubstituted rac-(5-phenylfuran-2-yl)-β-alanine ethyl ester, we u