33342-17-5

Basic information

• Product Name: 5-(4-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE
• Synonyms: 2-Furancarboxaldehyde,5-(4-fluorophenyl)-
• CAS NO: 33342-17-5
• Molecular Formula: C₁₁H₇FO₂
• Molecular Weight: 190.18
• Mol File: 33342-17-5.mol

Chemical Properties

• Boiling Point: 319°Cat760mmHg
• Flash Point: 146.7°C
• Appearance: /
• Density: 1.239g/cm³
• Vapor Pressure: 0.000348mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: 5-(4-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE(33342-17-5)
• EPA Substance Registry System: 5-(4-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE(33342-17-5)

Safety Data

• Hazardous Substances Data: 33342-17-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-(4-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE is used as a key intermediate in organic synthesis for the production of various chemical compounds. Its presence as a furan derivative with a reactive aldehyde group allows for multiple types of chemical reactions, facilitating the creation of a diverse range of molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 5-(4-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE is utilized as a starting material for the synthesis of complex molecules with potential biological and pharmaceutical activities. Its unique structure contributes to the development of new drugs, particularly those targeting specific biological pathways or diseases.
Used as a Reagent in Chemical Reactions:
5-(4-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE also serves as a reagent in a variety of chemical reactions, enabling the modification and functionalization of other molecules. Its reactivity, particularly due to the aldehyde group, is instrumental in these processes, making it a useful tool in the synthesis of new compounds with desired properties.
Used in the Development of Biologically Active Molecules:
5-(4-FLUORO-PHENYL)-FURAN-2-CARBALDEHYDE is employed in the research and development of biologically active molecules, where its unique structure can be leveraged to create molecules with specific interactions with biological targets. This can lead to the discovery of new therapeutic agents or probes for biological research.

InChI:InChI=1/C11H7FO2/c12-9-3-1-8(2-4-9)11-6-5-10(7-13)14-11/h1-7H

Upstream product

• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 27329-70-0 5-formylfurane-2-boronic acid 
• 352-34-1 4-fluoro-1-iodobenzene 
• 437-29-6 tris(4-fluorophenyl)bismuthane 
• 98-01-1 furfural 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 1765-93-1 4-fluoroboronic acid 
• 698-63-5 5-nitrofurane-2-carboxaldehyde 
• 371-41-5 4-Fluorophenol 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 57666-82-7 5-(4-Fluoro-phenyl)-furan-2-carbaldehyde oxime 
• 931376-00-0 1-(5-(4-fluorophenyl)furan-2-yl)-N-(piperidin-4-ylmethyl)methanamine 

Relevant articles and documents

New benzimidazolium N-heterocyclic carbene precursors and their related Pd-NHC complex PEPPSI-type: Synthesis, structures, DFT calculations, biological activity, docking study, and catalytic application in the direct arylation

New benzhydryl-5,6-dimethyl-(3-methylbenzyl)benzimidazolium salt as N-heterocyclic carbene precursors and their related new Pd-NHC complex PEPPSI-type with the general formula [PdBr2(NHC)(pyridine)] were prepared and theoretically studied. Quan

Synthesis, structures, DFT calculations, and catalytic application in the direct arylation of five-membered heteroarenes with aryl bromides of novel palladium-N-heterocyclic carbene PEPPSI-type complexes

A new series of Pd-catalysts based on an N-heterocyclic carbene PEPPSI-type ligand (PEPPSI = pyridine enhanced precatalyst preparation stabilization and initiation) with the general formula [Pd(ii)Br2(NHC)(pyridine)] was synthesized and fully characterize

Virtual screening-driven discovery of dual 5-HT6/5-HT2A receptor ligands with pro-cognitive properties

A virtual screening campaign aimed at finding structurally new compounds active at 5-HT6R provided a set of candidates. Among those, one structure, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (1, 5-HT6R Ki = 91 nM), was selected as a hit for further optimization. As expected, the chemical scaffold of selected compound was significantly different from all the serotonin receptor ligands published to date. Synthetic efforts, supported by molecular modelling, provided 43 compounds representing different substitution patterns. The derivative 42, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (5-HT6R Ki = 25, 5-HT2AR Ki = 32 nM), was selected as a lead and showed a good brain/plasma concentration profile, and it reversed phencyclidine-induced memory impairment. Considering the unique activity profile, the obtained series might be a good starting point for the development of a novel antipsychotic or antidepressant with pro-cognitive properties.

Novel N-Substituted oseltamivir derivatives as potent influenza neuraminidase inhibitors: Design, synthesis, biological evaluation, ADME prediction and molecular docking studies

The discovery of novel potent neuraminidase (NA) inhibitors remains an attractive approach for treating infectious diseases caused by influenza. In this study, we describe the design and synthesis of novel N-substituted oseltamivir derivatives for probing the 150-cavity which is nascent to the activity site of NA. NA inhibitory studies showed that new derivatives demonstrated the inhibitory activity with IC50 values at nM level against NA of a clinical influenza virus strain. Moreover, the in silico ADME predictions showed that the selected compounds had comparable properties with oseltamivir carboxylate, which demonstrated the druggablity of these derivatives. Furthermore, molecular docking studies showed that the most potent compound 6f and 10i could adopt different modes of binding interaction with NA, which may provide novel solutions for treating oseltamivir-resistant influenza. Based on the research results, we consider that compounds 6f and 10i have the potential for further studies as novel antiviral agents.

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.

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.

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.

Identification of a small molecule inhibitor that stalls splicing at an early step of spliceosome activation

Small molecule inhibitors of pre-mRNA splicing are important tools for identifying new spliceosome assembly intermediates, allowing a finer dissection of spliceosome dynamics and function. Here, we identified a small molecule that inhibits human pre-mRNA splicing at an intermediate stage during conversion of pre-catalytic spliceosomal B complexes into activated Bact complexes. Characterization of the stalled complexes (designated B028) revealed that U4/U6 snRNP proteins are released during activation before the U6 Lsm and B-specific proteins, and before recruitment and/or stable incorporation of Prp19/CDC5L complex and other Bact complex proteins. The U2/U6 RNA network in B028 complexes differs from that of the Bact complex, consistent with the idea that the catalytic RNA core forms stepwise during the B to Bact transition and is likely stabilized by the Prp19/CDC5L complex and related proteins. Taken together, our data provide new insights into the RNP rearrangements and extensive exchange of proteins that occurs during spliceosome activation.

Antibacterial and antifungal properties of guanylhydrazones

A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus A

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.