99113-89-0

Usage

Uses

Used in Pharmaceutical Industry:
5-(2,5-Dichlorophenyl)furfural 96 is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to contribute to the development of new drugs with potential therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 5-(2,5-Dichlorophenyl)furfural 96 is utilized as a precursor in the production of pesticides and other agrochemicals, enhancing crop protection and yield.
Used in Organic Synthesis:
5-(2,5-Dichlorophenyl)furfural 96 is used as a building block in organic synthesis for creating a wide range of organic compounds, showcasing its versatility in chemical reactions and the potential for diverse applications across various industries.
Used in Chemical Research:
As a chemical compound with unique properties, 5-(2,5-Dichlorophenyl)furfural 96 is employed in research settings to explore new chemical reactions, mechanisms, and the development of innovative materials and compounds.

InChI:InChI=1/C11H6Cl2O2/c12-7-1-3-10(13)9(5-7)11-4-2-8(6-14)15-11/h1-6H

Upstream product

• 98-01-1 furfural 
• 106-46-7 para-dichlorobenzene 
• 95-82-9 2,5 dichloroaniline 
• 27329-70-0 5-formylfurane-2-boronic acid 
• 29682-41-5 2,5-dichloroiodobenzene 
• 50-79-3 2,5-dichlorobenzoic acid 
• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 135145-90-3 2,5-dichlorobenzeneboronic acid 

Downstream Products

• 1427538-12-2 4-((5Z)-5-{[5-(2,5-dichlorophenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)butanoic acid 
• 1427538-15-5 2-((5Z)-5-{[5-(2,5-dichlorophenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)butanoic acid 

Relevant academic research and scientific papers

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.

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.

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.]

Palladium-catalyzed decarboxylative C-H bond arylation of furans

A Pd/PCy3/Ag2CO3 (Cy = cyclohexyl) catalytic system was found to promote decarboxylative arylation through the combination of decarboxylation and C-H bond functionalization. This protocol features a good substrate scope of

SAR analysis of innovative selective small molecule antagonists of sphingosine-1-phosphate 4 (S1P4) receptor

Recent evidence suggests an innovative application of chemical modulators targeting the S1P4 receptor as novel mechanism-based drugs for the treatment of influenza virus infection. Modulation of the S1P4 receptor may also represent an alternative therapeutic approach for clinical conditions where reactive thrombocytosis is an undesired effect or increased megakaryopoiesis is required. With the exception of our recent research program disclosure, we are not aware of any selective S1P4 antagonists reported in the literature to date. Herein, we describe complementary structure-activity relationships (SAR) of the high-throughput screening (HTS)-derived hit 5-(2,5-dichlorophenyl)-N-(2,6-dimethylphenyl)furan-2- carboxamide and its 2,5-dimethylphenyl analog. Systematic structural modifications of the furan ring showed that both steric and electronic factors in this region have a significant impact on the potency. The furan moiety was successfully replaced with a thiophene or phenyl ring maintaining potency in the low nanomolar range and high selectivity against the other S1P receptor subtypes. By expanding the molecular diversity within the hit-derived class, our SAR study provides innovative small molecule potent and selective S1P 4 antagonists suitable for in vivo pharmacological validation of the target receptor.

Arylation of Aromatic Heterocycles with Arenes and Palladium(II) Acetate

Treatment of aromatic heterocycles such as furfural, 2-acetylfuran, 2-formylthiophene, 2-acetylthiophene, 1-benzoylpyrrole, 1-(2,6-dichlorobenzoyl)pyrrole, 1-acetylindole, and 1-acetyl-3-methylindole with arenes and palladium(II) acetate gave the corresponding aryl-substituted aromatic heterocycles.