22078-59-7

Usage

Uses

Used in Chemical Synthesis:
5-(3-Chlorophenyl)-2-furaldehyde is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique molecular structure allows for further functionalization and modification, making it a versatile building block in organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-(3-chlorophenyl)-2-furaldehyde is used as a starting material for the development of new drugs with potential therapeutic applications. Its chemical properties enable the creation of novel molecular structures that can target specific biological pathways, offering new treatment options for various diseases and conditions.
Used in Material Science:
5-(3-Chlorophenyl)-2-furaldehyde can also be utilized in the development of advanced materials, such as polymers and coatings, due to its reactive functional groups and compatibility with various polymerization techniques. Its incorporation into these materials can enhance their properties, such as stability, durability, and resistance to environmental factors.
Used in Flavor and Fragrance Industry:
Due to its aromatic nature, 5-(3-chlorophenyl)-2-furaldehyde can be employed in the flavor and fragrance industry as a component in the creation of unique scents and flavors. Its distinct chemical structure can contribute to the development of novel fragrances and taste profiles, adding value to consumer products.
Used in Research and Development:
5-(3-Chlorophenyl)-2-furaldehyde serves as an important research tool in academic and industrial laboratories, where it can be used to study various chemical reactions and mechanisms. Its unique properties make it an attractive candidate for exploring new synthetic routes, understanding reaction kinetics, and developing innovative applications in various fields.

InChI:InChI=1/C11H7ClO2/c12-9-3-1-2-8(6-9)11-5-4-10(7-13)14-11/h1-7H

Upstream product

• 2689-65-8 5-iodofuran-2-carbaldehyde 
• 108-90-7 chlorobenzene 
• 98-01-1 furfural 
• 108-42-9 3-chloro-aniline 
• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 27329-70-0 5-formylfurane-2-boronic acid 
• 625-99-0 3-iodochlorobenzene 
• 33756-91-1 tris(3-chlorophenyl)bismuthane 
• 108-37-2 1-bromo-3-chlorobenzene 
• 63503-60-6 3-chlorophenylboronic acid 

Downstream Products

• 937807-66-4 2-(5-(3-chlorophenyl)furan-2-yl)-4,5-bis(4-methoxyphenyl)-1H-imidazole 
• 851340-16-4 3-[5-(3-chloro-phenyl)-furan-2-yl]-acrylic acid methyl ester 
• 1032383-17-7 trans-2-[2-[5-(3-chlorophenyl)furan-2-yl]vinyl]-1-methylpyridinium iodide 
• 851304-54-6 3-((5Z)-5-{[5-(3-chlorophenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)propanoic acid 
• 1004111-41-4 (Z)-3-((1H-benzimidazol-2-yl)methyl)-5-((5-(3-chlorophenyl)furan-2-yl)methylene)-2-thioxothiazolidin-4-one 
• 1004111-33-4 C₁₈H₁₄ClNO₅S 
• 1004111-29-8 C₁₇H₁₃ClN₂O₄S 
• 1004111-31-2 C₁₈H₁₄ClNO₄S₂ 
• 1004111-37-8 C₁₈H₁₅ClN₂O₅ 
• 1004111-32-3 C₁₈H₁₅ClN₂O₄S 

Relevant academic research and scientific papers

Carbon–Carbon Bond Formation for the Synthesis of 5-Aryl-2-Substituted Furans Catalyzed by K3[Fe(CN)6]

An efficient method for the carbon–carbon bond formation at C-5 position of 2-substituted furans to provide a range of π-diverse 5-aryl-2-substituted furan derivatives in 58–80% yield has been reported. The method employs several advantages such as use of catalytic amount of K3[Fe(CN)6] under mild conditions and short reaction time with high yields. Also, a variety of anilines with a variety of functional groups can be employed for the synthesis of 5-aryl-2-substituted furans. Graphic Abstract: [Figure not available: see fulltext.]

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.

Derivatives of (R)-3-(5-Furanyl)carboxamido-2-aminopropanoic Acid as Potent NMDA Receptor Glycine Site Agonists with GluN2 Subunit-Specific Activity

NMDA receptors mediate glutamatergic neurotransmission and are therapeutic targets due to their involvement in a variety of psychiatric and neurological disorders. Here, we describe the design and synthesis of a series of (R)-3-(5-furanyl)carboxamido-2-am

Novel Furan-2-yl-1 H-pyrazoles Possess Inhibitory Activity against α-Synuclein Aggregation

A series of novel furan-2-yl-1H-pyrazoles and their chemical precursors were synthesized and evaluated for their effectiveness at disrupting α-synuclein (α-syn) aggregation in vitro. The compounds were found to inhibit α-syn aggregation with efficacy comp

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.

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.

Discovery of selective protein arginine methyltransferase 5 inhibitors and biological evaluations

Protein arginine methyltransferase 5 (PRMT5) is an important protein arginine methyltransferase that catalyzes the symmetric dimethylation of arginine resides on histones or non-histone substrate proteins. It has been thought as a promising target for many diseases, particularly cancer. Despite the potential applications of PRMT5 inhibitors in cancer treatment, very few of PRMT5i have been publicly reported. In this investigation, virtual screening and structure–activity relationship studies were carried out to discover novel PRMT5i, which finally led to the identification of a number of new PRMT5i. The most active compound, P5i-6, exhibited a considerable inhibitory potency against PRMT5 with an IC50 value of 0.57?μm, and a high selectivity for PRMT5 against other tested PRMTs. It displayed a very good antiviability activity against two colorectal cancer cell lines, HT-29 and DLD-1, and one hepatic cancer cell line, HepG2, in a sensitivity assay against 36 different cancer cell lines. Western blot assays indicated that P5i-6 selectively inhibited the symmetric dimethylations of H4R3 and H3R8 in DLD-1 cells. Overall, P5i-6 could be used as a chemical probe to investigate new functions of PRMT5 in biology and also served as a good lead compound for the development of new PRMT5-targeting therapeutic agents.

Synthesis and antibacterial evaluation of furan derivatives bearing a rhodanine moiety

Two series of furan derivatives bearing a rhodanine moiety (4a-l and 5a-l) have been synthesized, characterized, and evaluated for their antibacterial activity. The majority of these compounds showed potent levels of inhibitory activity against a variety of different Gram-positive bacteria, including multidrug-resistant clinical isolates, with minimum inhibitory concentration (MIC) values in the range of 2-16 μg/mL. In particular, compound 4l was found to be the most potent of the synthesized compounds against the multidrug-resistant strains, with a MIC value of 2 or 4 μg/mL. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 μg/mL. An examination of the cytotoxicities of these agents revealed that they displayed low levels of toxicity toward HeLa cells. All of the compounds synthesized in the current paper were characterized by 1H and 13C NMR, infrared, and mass spectroscopy. Graphical Abstract: Two novel series of furan derivatives bearing a rhodanine moiety were synthesized, and evaluated for their antibacterial activity. Compounds 4l and 5a presented high potency against several multidrug-resistant clinical isolates.[Figure not available: see fulltext.]