19247-87-1

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 4-(5-FORMYL-2-FURYL)BENZOATE is used as an intermediate in the synthesis of various pharmaceuticals for its potential biological and pharmacological activities, contributing to the development of new drugs and therapeutic agents.
Used in Flavor and Fragrance Industry:
ETHYL 4-(5-FORMYL-2-FURYL)BENZOATE is used as a flavoring agent to enhance the taste and aroma of food products, as well as in the production of perfumes and cosmetics, where its aromatic nature adds to the sensory experience of these products.
Used in Chemical Research:
ETHYL 4-(5-FORMYL-2-FURYL)BENZOATE is used as a subject of interest in chemical research for its potential applications in the development of new organic compounds and the exploration of its properties and reactions in various chemical processes.

InChI:InChI=1/C14H12O4/c1-3-17-14(15)11-6-4-10(5-7-11)12-8-9-13(16-2)18-12/h2,4-9H,3H2,1H3

Upstream product

• 98-01-1 furfural 
• 94-09-7 p-aminoethylbenzoate 
• 2028-79-7 4-(ethoxycarbonyl)benzenediazonium chloride 
• 2689-65-8 5-iodofuran-2-carbaldehyde 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 131379-16-3 4-(ethoxycarbonyl)phenylzinc iodide 
• 27329-70-0 5-formylfurane-2-boronic acid 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 4334-88-7 p-ethoxycarbonylphenylboronic acid 

Downstream Products

• 57666-75-8 5-(4'-ethoxycarbonylphenyl)furan-2-carbaldehyde oxime 
• 84137-87-1 4-{5-[(E)-2-(1,4-Dioxy-quinoxalin-2-yl)-vinyl]-furan-2-yl}-benzoic acid ethyl ester 
• 57666-76-9 4-(5-Cyano-furan-2-yl)-benzoic acid ethyl ester 
• 1007580-58-6 ethyl 4-[5-({[2-(3-fluorophenyl)ethyl]amino}methyl)-2-furanyl]benzoate 
• 445458-94-6 ethyl 4-(5-((1-(4-(methoxycarbonyl)phenyl)-3,5-dioxopyrazolidin-4-ylidene)methyl)furan-2-yl)benzoate 
• 932953-77-0 4-(5-((benzylamino)methyl)furan-2-yl)benzoic acid 

Relevant academic research and scientific papers

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.

2. 5 - Double-substituted furyl derivatives and their use as SIRT protein inhibitor in the preparation of medicaments

The invention of the formula (I) indicated by the 2, 5 - disubstituted furan derivatives, the 2, 5 - disubstituted furan derivatives is mainly 2 - substituted amine, 5 - substituted phenyl, also discloses the preparation of the compounds and as SIRT prote

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.

Highly functionalized biaryls via Suzuki-Miyaura cross-coupling catalyzed by Pd@MOF under batch and continuous flow regimes

A diverse set of more than 40 highly functionalized biaryls was synthesized successfully through the Suzuki-Miyaura cross-coupling reaction catalyzed by Pd nanoparticles supported in a functionalized mesoporous MOF (8 wt% Pd@MIL-101(Cr)-NH2). This could be achieved under some of the mildest conditions reported to date and a strong control over the leaching of metallic species could be maintained, despite the presence of diverse functional groups and/or several heteroatoms. Some of the targeted molecules are important intermediates in the synthesis of pharmaceuticals and we clearly exemplify the versatility of this catalytic system, which affords better yields than currently existing commercial procedures. Most importantly, Pd@MIL-101-NH2 was packed in a micro-flow reactor, which represents the first report of metallic nanoparticles supported on MOFs employed in flow chemistry for catalytic applications. A small library of 11 isolated compounds was created in a continuous experiment without replacing the catalyst, demonstrating the potential of the catalyst for large-scale applications.

5-substituted-2-furaldehydes: A synthetic protocol utilizing an organozinc route

Facile synthetic routes for the preparation of a wide range of 5-substituted 2-furaldehydes have been revealed. They were accomplished through either Pd-catalyzed cross-coupling reaction of various aryl- and heteroarylzinc halides with 5-bromo-2-furaldehyde or utilization of a new organozinc reagent, 5-(1,3-dioxolan-2-yl)-2-furanylzinc bromide, which was easily prepared by the direct insertion of highly active zinc to 2-(5-bromofuran-2-yl-1,3-dioxolane. Of special note is the uniqueness of using a new organozinc reagent, representing a first example of the direct synthesis of the corresponding organozinc halide. The subsequent coupling reactions in various types of reaction conditions led to the formation of somewhat different furan derivatives. It is also of significance that all of the cross-coupling reactions were carried out under mild conditions.

Development of a novel class of B-RafV600E-selective inhibitors through virtual screening and hierarchical hit optimization

Oncogenic mutations in critical nodes of cellular signaling pathways have been associated with tumorigenesis and progression. The B-Raf protein kinase, a key hub in the canonical MAPK signaling cascade, is mutated in a broad range of human cancers and especially in malignant melanoma. The most prevalent B-RafV600E mutant exhibits elevated kinase activity and results in constitutive activation of the MAPK pathway, thus making it a promising drug target for cancer therapy. Herein, we describe the development of novel B-RafV600E selective inhibitors via multi-step virtual screening and hierarchical hit optimization. Nine hit compounds with low micromolar IC 50 values were identified as B-RafV600E inhibitors through virtual screening. Subsequent scaffold-based analogue searching and medicinal chemistry efforts significantly improved both the inhibitor potency and oncogene selectivity. In particular, compounds 22f and 22q possess nanomolar IC 50 values with selectivity for B-RafV600Ein vitro and exclusive cytotoxicity against B-RafV600E harboring cancer cells.

A convenient synthesis of 5-aryl- and 5-heteroaryl-2-furaldehydes by the cross-coupling reaction of organozincs

An efficient synthetic route for the preparation of 5-heteroaryl- and 5-aryl-2-furaldehydes has been developed. It has been accomplished by the palladium(0)-catalyzed cross-coupling reaction of heteroarylzinc and arylzinc reagents with 5-bromo-2-furaldehyde under very mild conditions.

C-H and C-Si functionalization of furan derivatives: Palladium-catalyzed homocoupling and arylation reactions

Palladium-catalyzed arylation reactions of benzofuran derivatives are shown to take place at the carbon - hydrogen bond or carbon - silicon bond adjacent to the oxygen atom. A variety of furan derivatives are obtained in good yields. Georg Thieme Verlag S

Preparation of aryl and heteroaryl indium(III) reagents by the direct insertion of indium in the presence of LiCl

Sensitive functional groups, including ketone, aldehyde, and ester groups, may be present in aryl indium reagents prepared in good to excellent yields by the treatment of aryl and heteroaryl iodides with indium powder in the presence of LiCl (see example)

Discovery of a potent CDK2 inhibitor with a novel binding mode, using virtual screening and initial, structure-guided lead scoping

Virtual screening against a pCDK2/cyclin A crystal structure led to the identification of a potent and novel CDK2 inhibitor, which exhibited an unusual mode of interaction with the kinase binding motif. With the aid of X-ray crystallography and modelling,